72 Hours In: The Hamptons

72 Hours In: The Hamptons

Between its white sand beaches, vibrant Atlantic sunsets, and buzzing social scene, there’s no place quite like the Hamptons for a long-weekend getaway. Here, New England beach town charm meets urban sophistication, long-time locals mingle among celebrity homeowners, and city dwellers are in good company as they escape the metropolitan bustle for a few days to savor the stylish serenity of this Long Island haven.

There’s something for everyone among the 20 or so distinct villages in the Hamptons, each with its own personality. Visitors will find both laid-back, countryside-inspired hideaways on the beach and lively destinations filled with five-star restaurants, shopping, and nightlife.

With so much to discover, bypass much of the oft-maligned city traffic and fly directly into the Hamptons to spend more time enjoying what makes the East End such a beloved retreat. Tradewind offers charter flights to East Hampton Airport, Montauk Airport, and Westhampton Beach Airport, all providing convenient access to the Hamptons’ top towns.

After your flight touches down, experience the best of the area with this 72-hour Hamptons itinerary.

Day One

Begin your getaway in East Hampton, one of the area’s most popular hamlets and a hub for some of the East End’s best dining, shopping, and nightlife. After renting a car (or hiring a car service), check into The Baker House 1650, a luxury inn within walking distance of the main town and beach. While the Hamptons is known for summer-long rentals and vacation homes, upscale bed and breakfast-inspired accommodations like these offer an alternative for weekend visitors, providing a taste of a historic Hamptons home stay with the amenities of a high-end hotel.

Photo: The Baker House 1650

Photo: The Baker House 1650

Spend some time settling into The Baker House 1650 to enjoy the property’s 17th-century architecture, lush grounds, and three pools, then wander down Main Street to explore East Hampton’s shops. You’ll find both classic outposts and high-end boutiques, from chic swimwear at Vilebrequin to your next beach read at the ever-charming BookHampton

Photo: BookHampton

Photo: BookHampton

After a bit of retail therapy, head toward Bridgehampton for an early afternoon reservation at the tasting room at Wölffer Estate. Perhaps best known for their aptly named Summer in a Bottle rosé, guests can sample a variety of wines alongside gourmet small plates and charcuterie boards, all set to sweeping vineyard views.

After your afternoon of wine tasting, make your way to Bridgehampton’s lively Main Street to wander among shingled buildings and boutiques. While you’re there, those interested in dessert before dinner should stop by the iconic Candy Kitchen, lauded throughout the Hamptons for their decadent homemade ice cream selection.

Make a reservation ahead of time for dinner at Jean-Georges at Topping Rose House, crafting contemporary farm-to-table cuisine in one of the Hamptons’ most elegant hotels. The famed chef’s menu sources local ingredients from the area’s farmers and fishermen, as well as produce grown on the property’s one-acre farm.

Day Two

Begin your day with a workout at one of the Hamptons’ many trendy fitness studios — SoulCycle, Flywheel, AKT, Erika Bloom Pilates, and Tracy Anderson all have outposts in East Hampton, or you can take a class at Barry’s Bootcamp in nearby Amagansett. For a lighter activity, head over to the East Hampton Main Beach on one of The Baker House 1650’s bikes for rent, then kick your shoes off for a morning walk on the sand.

Photo: Dr Smood

Photo: Dr Smood

Refuel with a green juice at health-conscious café Dr Smood in East Hampton, then take a short drive north to the town of Sag Harbor. As an old whaling town, quaint colonial-era architecture lines the main street and smaller, family-run shops triumph over big-name brands.

For lunch (or brunch) after a stroll through the town, enjoy panoramic harbor views paired with locally sourced dishes at The Restaurant at Baron’s Cove. Beautifully renovated in 2015, Baron’s Cove is known by many as Sag Harbor’s most stylish hotel, offering sleek beach house-inspired design, a saltwater pool, and a happening lounge and dining scene. If you find yourself in Sag Harbor later in the evening, you can also sit down for dinner on the water at local favorite Beacon, open only during the summer.

Photo: Baron’s Cove

Photo: Baron’s Cove

Otherwise, make your way back to East Hampton for an afternoon of R&R. Unwind by the pool or at the spa at The Baker House 1650, or take your bike back to the beach, reveling in the relaxed pace of Hamptons living. For dinner, make a reservation at Hamptons mainstay Nick & Toni’s, offering rustic Northern Italian cuisine in a farmhouse setting (that’s also likely playing host to at least a celebrity or two on any given night).

Day Three

Though spending free time at one of the Hamptons’ many beaches is highly encouraged throughout your entire stay, dedicating a few uninterrupted hours to lounging out on the sands is a must. The Baker House 1650 offers East Hampton Main Beach parking passes to guests (which are required), as well as umbrellas and chairs to unwind on. But first, stop by Cavaniola's Gourmet in Amagansett for all the fixings of a perfect beach picnic, from cheeses to paninis (it’s one of chef Ina Garten’s favorite local stops).

Photo : Section215 via Flickr / CC BY

Photo: Section215 via Flickr / CC BY

In the afternoon, take a drive up to Montauk. This fishing village has become a Hamptons hotspot in recent years, seeing an influx of dining, nightlife, and hospitality offerings. Fondly referred to as “the End of the World,” Montauk is perched on the easternmost tip of Long Island, and its expansive Atlantic views are best seen from the historic Montauk Lighthouse. Climb 137 iron steps for a high-up vantage, or find a perfect spot on the grounds to frame a picturesque lighthouse photograph.

Because no trip to the Hamptons is complete without a decadent lobster roll, stop at the eponymous Lobster Roll in Amagansett on your way back, commonly referred to as Lunch thanks to its iconic glowing sign. There’s little argument over its status as the best lobster roll in Long Island (if not one of the best in the world). As the sun dips into the Atlantic, it’s the perfect way to cap off an idyllic weekend in the Hamptons.

Photo: The Lobster Roll

Photo: The Lobster Roll

Featured photo: Sue via Flickr / CC BY


Tradewind offers private charter flights to East Hampton (HTO), Montauk (MTP), and West Hampton Beach (FOK) year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

A Weekend Ramble Through The Berkshires’ North County

A Weekend Ramble Through The Berkshires’ North County

On the western edge of Massachusetts, Berkshire County stretches north-south for 60 miles, from the Vermont border to the Connecticut state line. Its vast beauty is too much territory to cover in a long weekend—but thankfully, visitors don’t have to.

The excitement has been traditionally clustered at the southern end, framed by the four towns of Lenox, Becket, Great Barrington, and West Stockbridge. But now, so-called “North County” is equally as compelling.

Pointing the compass northward affords visitors a unique look at the natural splendor and history of the Berkshires. The geographical center of this up-county area is the sigh-inducing college hamlet of Williamstown, which is flanked by a pair of little cities, Pittsfield and North Adams, each artfully reborn out of a faded industrial past.

Photo: Hotel on North

Photo: Hotel on North

Begin your loop at the compact Pittsfield Municipal Airport—transfer there from your Tradewind flight to a well-appointed rental SUV, and in just minutes, you will have pulled up at Hotel on North, a 45-room boutique hotel that became the beating heart of Pittsfield’s downtown from the day it opened in 2015. A former menswear and sporting goods emporium, the building today is a tour de force of preservation-based remodeling, its good bones exposed and its interiors jazzed up with repurposed trim elements from the distant past. The hotel’s highly popular restaurant, Eat on North, is run by former White House chef Ron Reda.

Take the evening and part of the next day to ramble Pittsfield’s downtown and decide whether all those “Brooklyn of the Berkshires” claims are well-deserved. From District Kitchen and Bar on West Street up to Methuselah at the corner of North and Bradford to the tapas and wine bar Mission a block away, the town’s dining and drinking options invoke rustic-chic sophistication among old-city walkability. Boutiques and retro shops are in abundance, including such favorites as the décor-centric Dory and Ginger, Steven Valenti’s Clothing, and the Berkshire General Store. Morning coffee and first-rate baked goods are steps away at Dottie’s coffee shop, which also boasts the kind of meeting-place vibe that convinces people to move to resurgent communities like this.

Photo: Mission Berkshires

Photo: Mission Berkshires

Route 8 out of Pittsfield takes you along the eastern edge of the 12,000-acre Mount Greylock State Reservation. It’s named for the state’s highest peak and laced with upland trails that will carry a hiker deep into the heart of a New England summer. On this trip, you may want to stop by the visitor center and pick up a trail map, in case you’re inspired to plan an outdoorsy return to the area amid October’s cooler air and bonfire-hued foliage. If you opt to skip the park and cruise directly from Pittsfield to North Adams, you’ll be there in less than 30 minutes most days.

What you’ll find on arrival is a pocket-sized city, still somewhat in recovery from a mid-1980s economic blow — but blooming back to life with plenty of charm. Today, the largest museum of contemporary art in the U.S., the Massachusetts Museum of Contemporary Art (or Mass MoCA), occupies a 24-acre campus originally built by Sprague Electric, the space-mission contractor that supplied NASA and other federal agencies with advanced circuitry and components till its closure (leading to the town’s aforementioned economic downturn).

Photo: Mass MoCA via Grace Clark

Photo: Mass MoCA via Grace Clark

To display the works produced by contemporary art superstars like Sol LeWitt, Laurie Anderson, and Robert Rauschenberg takes vast amounts of inexpensive space — much more than the name-brand museums in big cities have available, but perfectly suited for this unlikely space in The Berkshires. Combine the need for acreage with creative vision, and you’ve got a gritty town fast on the rise whose principal industry is modern art. Odd as that may sound, Mass MoCA reportedly boosted local economic activity by $51 million in 2017 alone.

You soak up the “anything’s possible” zen of North Adams by staying at The Porches, a chic hotel on the Mass MoCA property, or perhaps at the brand-new Tourists, a self-styled “riverside retreat inspired by the classic American roadside motor lodge.” Investors from the California foodie scene designed and built Tourists and its food-and-beverage amenities, featuring a new lounge, The Airport Rooms, serving classic cocktails and a “creative roadhouse” menu. Its executive chef, Corey Wentworth, was recruited from Boston’s Flour Bakery.

Photo:  Tourists via Peter Crosby

Photo: Tourists via Peter Crosby

The artwork at Mass MoCA is vast in scale, which means you go through it more than past it, which makes the appreciation experience looser and more fun. Performing arts further increase the hip factor here — there are film screenings, rock concerts, comedy festivals, and other on-stage exuberance. The beloved and versatile band Wilco has a particular footprint at Mass MoCA, most notably thanks to its biennial Solid Sound Festival — this year, the Wilco event happens June 28th through 30th.

Also on campus is Bright Ideas Brewing, a craft brewery and taproom. Meanwhile, any left or right you take in the general vicinity of the campus will reveal some semi-pro mural or sculpture to echo the crown jewels of the museum. Admittedly, most of us lack the endurance to study art for entire mornings or afternoons — but that’s not the point here. A day in North Adams is actually akin to life inside a “60 Minutes” segment, with socioeconomic and cultural history being made in real time. (If you’re quiet, you can hear the property values rising.)

Fifteen minutes east is prim, prosperous Williamstown, where the top-ranked liberal arts college in the country (per U.S. News) seamlessly merges its verdant campus with the commercial layout of the town. In the summer, the cultural scene around Williams College is ever vibrant. This season, the Broadway-quality dramatic offerings at the Williamstown Theater Festival include one play that’s particularly easy to recommend. It’s a revival of Henrik Ibsen’s Ghosts starring Golden Globe and Academy Award nominee Uma Thurman, on stage through most of August. Meanwhile, the Clark Art Institute has a high-powered French Impressionist exhibit, titled “Renoir: The Body, the Senses,” devoted to Renoir’s unsurpassed achievement in the depiction of body figures.

Photo: Mezze Bistro & Bar via FED Guides

Photo: Mezze Bistro & Bar via FED Guides

Dining in Williamstown won’t disappoint—perennial favorites include Mezze Bistro & Bar as well as The ‘6 House and Pub, a few minutes outside of town in a rural setting. The Water Street Grill is just right for high-quality tavern fare and live music. Tucked around the corner from Spring Street's shops, pubs, and restaurants is one of the half-dozen best public golf courses in all of New England, Taconic Golf Club. An early-20th-century classic by Stiles and Van Kleek, Taconic is owned by the college, meticulously maintained at all times and recently renovated by Gil Hanse, the most renowned course architect working today.

When your three-stop tour is over, it’s time to head south down historic Route 7 toward Pittsfield, enjoying sublime Berkshires scenery plus endless roadside attractions, from antiques to ice cream to riverfront picnic grounds. An easy hour’s ride on an old country highway, it’s ideal for reflecting on the artsy, urban fascination you’ve encountered while letting the innocence of rural New England summertime float by.


Tradewind offers private charter flights to the Berkshires year-round on a fleet of Pilatus PC-12s. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured Photo: Tourists via Nick Simonite

5 Iconic Fourth of July Celebrations in New England

5 Iconic Fourth of July Celebrations in New England

As the country’s bona fide birthplace, it’s only fitting that New England would be in a league of its own on Independence Day. Fourth of July is arguably the region’s most exciting holiday, marked by festive parades, all-American cookouts, and dazzling fireworks displays that light up the skies and reflect on the waters of the Atlantic.

From charming coastal celebrations to large-scale bashes, here’s where you can take in the best Fourth of July celebrations this summer, each accessible by Tradewind Aviation’s shuttle or charter flights.  

Nantucket, Massachusetts

Photo: Jamie Holmes

Photo: Jamie Holmes

Each year, Nantucket hosts a unique July 4th celebration among its Colonial-style buildings and picturesque beachfront. The hallmark of Nantucket’s Independence Day festivities is the annual water fight between Town of Nantucket’s Fire Department and the Boynton Lane Reserves, a tradition that began back in 1981 when local real estate broker H. Flint Ranney (who had acquired a 1927 LaFrance ladder truck) challenged Nantucket’s then-fire chief Bruce Watts to a friendly battle. The event has endured, and for its 38th year, visitors can make their way to Main Street at “high noon” to cool off (the festivities officially commence two hours early at 10am).

Following the water fight, children’s games begin at 5pm, including potato-sack races, three-legged races, wheelbarrow races, and tug-of-war, followed by live music on the bandstand at 6pm. Those arriving for the weekend are in luck — this year’s fireworks show will be held on Jetties Beach on Friday, July 5th.

Recommended Airport: Nantucket Memorial Airport (ACK) via Tradewind Shuttle or Tradewind Private Charter

Martha’s Vineyard, Massachusetts

While there are six main towns on the island of Martha’s Vineyard (each with their own distinct Fourth of July events), the community of Edgartown in particular stands out for its time-honored traditions. The day centers around a late-afternoon parade at 5pm, where onlookers watch as elaborate floats, antique cars, marching bands, and more travel down Main Street and its surroundings. For prime viewing opportunities, arrive early to claim a spot in the historic town center, known for its white Greek Revival-style architecture (which, ironically, feels quintessentially New England).

The festivities continue on the harbor with a fireworks show at dusk, best viewed from Memorial Wharf. Past years have also included the Martha’s Vineyard Preservation Trust’s annual barbecue on the lawn of the Dr. Daniel Fisher house on Main Street, featuring cookout classics from burgers to hot dogs. St. Elizabeth’s Church has been known for their lobster rolls during the afternoon, and live music has been held at Old Whaling Church.

Recommended Airports: Martha's Vineyard Airport (MVY) via Tradewind Shuttle or Private Charter; Katama Airpark (1B2) via Tradewind Private Charter 

Bar Harbor, Maine

Photo: BHCOC

Photo: BHCOC

An old-fashioned Fourth of July celebration can be found on Mount Desert Island in the town of Bar Harbor. Just off of Maine’s Down East shoreline, their festivities are regularly voted among the top Independence Day events in the country, and it’s not hard to see why, given the town’s seemingly endless things to do on the holiday.

The day commences with a blueberry pancake breakfast from 6am to 10am. Or, for a more athletic kick-off, runners can sign up for a 100-kilometer relay in teams of two to nine participants, with start times beginning at 6am. The race route offers a scenic overview of the rocky Maine seaside against the lush backdrop of Acadia National Park, along with every town and village on the island.  

Make sure to be back in time for the community parade through downtown Bar Harbor at 10am and the seafood festival at 11am, where fresh lobster, mussels, corn, and more are paired with an outdoor concert and followed by the annual lobster races (betting on your favorite crustacean is encouraged, as proceeds go toward the MDI YMCA Scholarship Program). The day also includes a nonprofit showcase, a craft fair and marketplace, and plenty of live music throughout the town, from Agamont Park to Bar Harbor Village Green. The festivities conclude with breathtaking fireworks over Frenchman Bay at 9:15pm.

Recommended Airport: Hancock County Bar Harbor Aiport (BHB) via Tradewind Private Charter

Bristol, Rhode Island

Known as “America’s most patriotic town,” Bristol, Rhode Island boasts the world’s first Fourth of July celebration, and its revelry has only grown in the 234 years that have passed. In true over-the-top fashion, the town doesn’t wait for July 4th to begin celebrating —  activities and events officially commence on June 14th with a Flag Day Ceremony. In the weeks that follow, local organizations hold events including a free concert series at Independence Park, the Bristol Stomp Block Dance on June 15th, the annual Fourth of July Ball on June 21st, the Bristol Independence Rhode Race Half Marathon on June 29th, and even a Patriotic Pet Photo Contest from June 17th -30th.

Rather than mark the end of the holiday, the town’s fireworks show is held on June 3rd at 9:30pm on Bristol Harbor, building excitement for Independence Day itself. The next morning, the town wakes to the churches’ Ringing of the Bells at 6am, followed by the Military, Civic, and Firemen’s parade at 10:30am, viewed by more than 200,000 onlookers. Blending small-town charm with grand spectacle, it’s an unforgettable gathering for both locals and visitors.

Recommended Airport: Newport State Airport (UUU) via Tradewind Private Charter 

Boston, Massachusetts

Photo: Michael Blanchard

Photo: Michael Blanchard

Boston is steeped in colonial history year-round, but its revolutionary beginnings are fully celebrated on the Fourth of July. The mayor starts with a speech at City Hall Plaza at 9am, and from there, a festive parade makes its way toward the Old State House, where a stirring reading of the Declaration of Independence takes place on the balcony. Recited by the Captain Commanding of the Ancient and Honorable Artillery Company of Massachusetts, it’s a meaningful annual tradition for the city of Boston as a reminder of the nation’s roots.

Before this tradition takes place, the parade stops at the Granary Burying Ground on Tremont Street for a fitting tribute to the founding fathers. Here, officials lay wreaths on the patriots’ graves, including John Hancock, Samuel Adams, and Robert Treat Paine.

The day’s entertainment culminates with the renowned Boston Pops Fireworks Spectacular. This free (and televised) orchestra concert at the Hatch Memorial Shell on the Charles River Esplanade begins at 8pm (though gates open at 9am for those dedicated to getting a seat). Led by famed Boston Pops conductor Keith Lockhart, this year’s event will also feature Queen Latifah, Arlo Guthrie, and more. The fireworks lend a dramatic, awe-inspiring touch at 10:30pm, closing out the evening with a bang.

Recommended Airport: Boston Logan International Airport (BOS) via Tradewind Private Charter

Up Close and Personal with Cape Cod’s Great White Sharks

Up Close and Personal with Cape Cod’s Great White Sharks

The ocean’s most feared apex predators, great white sharks, have triumphantly returned to Cape Cod and its surrounding islands. But there’s no need to cue the Jaws theme: While their return may not sound like good news to beachgoers in the Northeast, the sharks’ reestablished presence provides visitors a unique opportunity to experience these misunderstood, majestic creatures in an authentic and safe way.

The Atlantic White Shark Conservancy (AWSC) offers a number of ecotours designed to give the public a better understanding of the great white comeback (spurred by a rebound in the grey seal population), allowing them to see firsthand what scientists are doing to help man and shark peacefully coexist. AWSC’s most thrilling adventure? Its “Great White Shark Expedition,” a once-in-a-lifetime chance to get up close and personal with the Cape’s most notorious resident (and live to tell the tale).

Photo: Paul Rubio

Photo: Paul Rubio

No, this isn’t a controversial cage-diving experience like those common in South Africa, where waters are chummed and seal dummies are thrashed around to attract and excite the sharks. This is a research-based wildlife interaction in which participants shadow shark researchers as they tag, identify, and study great whites off the coast of Cape Cod.

In partnership with Chatham Bars Inn, AWSC runs the expeditions twice daily on Wednesdays, Thursdays, and Sundays from July 3rd to October 27th (weather permitting). Departing from the pier at Chatham Bars Inn and accompanied by a member of AWSC's team, a maximum of five guests head out into prime great white real estate. Sharks are detected using aerial surveys from the research team’s Cessna plane overhead, through shark receivers, and with AWSC’s Sharktivity app, which monitors the whereabouts and activity of previously tagged great white sharks in the area.

Once spotted, sharks are slowly approached, and a hydrophone is placed into the water to determine if the shark has already been tagged. If so, the shark’s coordinates are matched to the app. If not, scientists may attempt to tag the great white. In all cases, the sharks are identified — the team is on a first-name basis with most sharks, seeing them daily and already knowing each one’s personality traits. Observations are then logged by the team.

Photo: Paul Rubio

Photo: Paul Rubio

There are many purposes for this trip: First, you’ll witness conservation in action as scientists collect data used in behavioral and ecological studies of great whites. Next, you’ll get to participate first-hand in mitigating human-wildlife conflicts (the Sharktivity app uses the information gathered to send alerts to researchers and the public when tagged sharks get a little too close to the shoreline for comfort). Moreover, you’ll become an ambassador for helping debunk the myth of great whites as man-hungry villains. In fact, you’ll be stunned at how shy many of the great whites appear upon approach and how they go about their daily business along the Cape, rarely bothering beachgoers. (In fact, the latest shark attack stats from 2018 indicate a slim 1 in 3.75 million chance of being attacked.)

Of course, as this is nature, shark sightings are never guaranteed. That said, on Goodspeed’s particular Great White Shark Expedition, five were spotted at close range. If this experience sounds a little too intense, AWSC also offers one-hour “Receiver Excursions” on Mondays and Wednesdays from July 1st through September 2nd, 2019. On this trip, you’ll cruise around the seal-rich Chatham Harbor with AWSC staff, looking for signs of predation and analyzing data from a shark receiver and Sharktivity.

Photo: Paul Rubio

Photo: Paul Rubio

Another AWSC adventure to consider is the all-day “White Sharks and Whales” group expedition, where guests will seek out great whites plus humpback whales and seabirds. Taking place only twice per year, the trip leaves from Plymouth, Massachusetts and includes breakfast, lunch, and a souvenir T-Shirt. Dates this year are September 7th and Sept 14th, 2019. 

Whichever excursion sounds most exciting, visitors to Cape Cod shouldn’t miss out on their chance to play a role in the area’s great white shark comeback story.


Tradewind Aviation offers charter flights to Cape Cod year-round. Great White Shark Expeditions are $2,500 per boat for up to five passengers (most of this fee goes directly to research and is tax deductible). Receiver Excursions are $55 per person; White Sharks and Whales trips are $160 per person. To learn more and book your shark expedition, call AWSC at 1-800-527-4884. 

Featured Photo: AWSC

5 Bar Harbor Hikes to Explore the Rugged Beauty of Maine

5 Bar Harbor Hikes to Explore the Rugged Beauty of Maine

In the northeast corner of New England, Maine’s Down East shoreline is a rugged stretch of snaking inlets and lighthouse-studded peninsulas. (In fact, unfurled into a straight line, the state’s Atlantic border would total more miles than the entire California coast.) This vast seaside was carved out by a long-gone glacier, which also left a legacy of sprawling bays strewn with forest-covered islands.  

Among them is Mount Desert Island, the Down East’s crown jewel and home to its charming gateway town of Bar Harbor. Singular in its brand of natural beauty, this Northeast enclave is a stunning haven of mountain forests, colossal granite cliffs, and rocky coastline.

Fitting, then, that the island also features Acadia National Park, America’s first designated wilderness area east of the Mississippi — and its most visited today. It’s not hard to see the allure: The national park and its town are a sanctuary for over 40 species of native wildlife, and the island is laced with 125 miles of hike-able trails.

With at least 25 distinct hikes spanning every level of difficulty to choose from, here are five Mount Desert Island favorites. Make your way there on a Tradewind charter flight to Bar Harbor, and from there, the trailheads wait just a short distance from the town.

The Ocean Path

Photo   : Christian Collins via Flickr / CC BY

Photo: Christian Collins via Flickr / CC BY

For a leisurely stroll that’s filled with natural wonders, try the Ocean Path, which meanders along the coast for two miles between Sand Beach and Otter Point. With its flat, obstacle-free terrain, this paved path is one of the most family-friendly trails on the island.

No matter which direction you decide to take (the path is accessible from terminal parking lots on both the Beach and Point sides), this walk provides a captivating yet peaceful glimpse of coastal Bar Harbor. It’s beautiful in every weather condition, too — which is good news, considering it swaps daily (if not hourly) between sunshine and atmospheric fog.

Halfway through the walk is Thunder Hole, a unique fissure in the craggy rocks where the crashing waves transform into roaring geysers up to 40 feet high. Between this awe-inspiring spectacle and the tide pools of Otter Point, you’ll also find the bumpy cove of Boulder Beach, named for its collection of bowling ball-like rocks that have been smoothed out by the tumultuous Atlantic. Built up over centuries on the east-facing shore, they glow like a field of pink gumdrops with the rising sun.

Gorham Mountain Trail

Photo   : NPS/Victoria Stauffenberg via Wikimedia Commons / CC BY

Photo: NPS/Victoria Stauffenberg via Wikimedia Commons / CC BY

Close to the Ocean Path (just past Thunder Hole) is the entrance to Gorham Mountain Trail, a moderate hike that’s 525-foot summit offers scenic overlooks of the topography below and the adjacent peaks. As an added bonus during the summer, this jaunt is lined with vibrant Wild Maine blueberry bushes (so it’s no surprise that hikers can often be seen descending with purple-stained fingers).

Follow the route from the trailhead as it slopes gently up the side of the mountain through a spruce forest. When the trail forks, either way will get you to the top (they rejoin further ahead), but those looking for an easier path should veer left, where there are fewer natural hurdles.

Eventually, the woods will empty out into a beautiful clearing that’s often mistaken for the peak. Take some time here to soak in the views of the Otter Cliffs and Cranberry Islands before continuing to the true summit just ahead, complete with its own spectacular eagle-eye vantage of both land and sea.

Cadillac Mountain


Rising 1,528 feet above sea level, Cadillac Mountain is not only the tallest of Mount Desert Island’s 20 peaks; its summit is also the highest point along the North Atlantic seaboard. From October to March, the mountaintop is known as the first place in the United States to spot the rising sun.

There are multiple ways to reach Cadillac’s precipice and its panoramic views, and they vary in difficulty. Via the paved Cadillac Mountain Road, those with limited time or mobility can actually park at a lot near the top before walking its scenic, 0.3-mile loop. Alternatively, Cadillac’s winding road (which inclines gradually over 3.5 miles) can be easily navigated from the bottom.     

For less pavement and more trail, take the out-and-back North Ridge Trail, a moderately difficult but visually magnificent open ascent. To find the trailhead, park in the ME 233 lot (located a few miles west of Bar Harbor), head down Park Loop Road until you find Kebo Brook Trail, and follow it for less than half a mile. There, you’ll find the beginning of North Ridge Trail, making way for three picturesque miles to Cadillac’s pinnacle.    

A more strenuous path is the South Ridge Trail Loop. Toward the summit, the forested trail opens up to a granite face, and some boulder scrambling is required to conquer the steep slope. However, hikers are immediately rewarded with expansive views of the national park and the Atlantic, as well as the nearby Porcupine Islands perched in the foreground of Frenchman’s Bay, their hills bristling with pines.

Jordan Pond Path

Photo   : Naya Sriramaneni via Wikimedia Commons / CC BY

Photo: Naya Sriramaneni via Wikimedia Commons / CC BY

Tracing a 3.3-mile circuit around Acadia’s deepest (and second largest) lake is Jordan Pond Path. Though most of the loop is easy to navigate (transitioning between patchworks of flat ground and wood-plank walkways), this hike’s moderate difficulty comes as the path crawls across some uneven granite on the pond’s northwest side.

Hugging the shoreline, the trail teems with aquatic wildlife, including frogs, beavers, birds, and more. The path also offers plenty of stopping points to savor the surrounding mountains, which frame the placid pond from nearly every angle.

Take some extra time to look across the lake from its southern edge, which on clear days features the domed peaks of South and North Bubble Mountains rising over the water and reflecting on its glassy surface. To satisfy post-hike hunger, the south side of the lake is also home to Jordan Pond House, the national park’s only full-service restaurant, which has held wild acclaim for its popovers (served with butter and Maine strawberry jam) for at least the past 125 years.

Bubble Rock 

Photo   : Heidi via Wikimedia Commons / CC BY

Photo: Heidi via Wikimedia Commons / CC BY

While each of the twin Bubble Mountains on Jordan Pond’s north side has a unique pathway to its respective summit, the south peak is popular due to a peculiar landmark left behind long ago by a glacial retreat: Bubble Rock itself. Permanently perched on the side of a cliff, it’s seemingly on the brink of tumbling into the wilderness below.

To see the boulder up close, park in the Bubbles parking lot before taking the Bubbles Divide Trailhead west through the forest, where it cuts through the valley separating the north and south peaks. Soon after passing the North Bubble trail on the right side, the South Bubble trail will emerge on the left. Follow this easy path until it ascends to the summit, and look for the small side trail leading to Bubble Rock, plus breathtaking views of Jordan Pond from above.

When it’s time to head back down, those with children will want to backtrack using the same easy route. Others looking for a more adventurous descent can continue down the South Bubble Trail, which requires some clambering as it weaves in switchbacks down the cliffside, eventually joining up with Jordan Pond Path. 


Tradewind offers private charter flights to Bar Harbor year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured Photo: Christian Collins via Flickr / CC BY

A Golfer’s Pilgrimage to Fishers Island

A Golfer’s Pilgrimage to Fishers Island

A Tradewind flight across Long Island Sound to Fishers Island offers plenty of breathtaking East Coast views. But for golf aficionados soaring over the eastern end of the seahorse-shaped island, none are more spectacular than the golf perfection spread out below.

Just off the coast of Connecticut, Fishers Island Club opened in 1926 during what’s considered the golden age of course-building. One of the era’s most brilliant architects, Seth Raynor, designed a dozen-plus courses during this time that are still celebrated today — but you’d be justified to call this one his masterpiece. 

Among the experts echoing this view is Thomas Dunne, director of the Golfweek magazine course-rating panel and co-founder of literary golf journal McKellar. He considers Fishers Island to be “one of the 10 best properties for golf anywhere on Earth.”

There’s a section of the course, beginning with the par-4 4th hole, that Dunne finds particularly inspiring. “To me, it’s the greatest nine-hole run in the world,” he says, “if you combine the natural environment with the excellence of its design and construction.”


Gil Hanse, arguably the most sought-after course architect in the world these days, has played Fishers Island many times and finds it unsurpassed as a combination of stunning visuals and strategic subtlety.

“The first time you play it, you can’t appreciate it architecturally,” says Hanse, who designed the course for the 2016 Olympics in Rio de Janeiro. “There’s too much beauty to take in, too many water views — [the] Atlantic Ocean, Fishers Island Sound, [and] tidal marsh all frame what you see and tend to mask the complexity of the design.”

He’s talking in part about angles of play — the geometry at work as targets are chosen and a player balances risk-reward. “The third hole, a par-4, has an elevated fairway and a green very exposed to the wind,” Hanse says. “If one golfer opted to drive down the right side and his partner hit a drive down the left, they’d basically be playing two different golf holes — and you’ll find strategic variation like that throughout the round.”

You can’t write about a Seth Raynor course without mentioning the design “standards” or “template holes” he so loved. These have intriguing names like Redan, Eden, Punchbowl, Alps, Biarritz, Double Plateau, and Cape. Along with his mentor, Charles Blair Macdonald, Raynor made a habit of including architectural elements that pay homage to beloved golf holes on historic British courses.

Fishers Island embodies that philosophy in fine fashion. It’s even got an Alps-Punchbowl combination — dramatically high mounds guarding a large, bowl-shaped green that will mercifully kick an off-target shot back toward the flagstick.

Considering his legacy, it’s no surprise that there’s even a Seth Raynor Society. It’s administered by Anthony Pioppi, a writer and course expert who recently published the book The Finest Nines: The Best Nine-Hole Golf Courses in North America.


In the name of participatory journalism, Pioppi made the mid-life decision to caddie on Fishers Island for several summers, during which he absorbed the quirks and cadences of life “seven miles from reality,” as he and others have described the island.

“People there are genuinely friendly, and part of that is because everyone crosses paths everywhere,” says Pioppi. “There are two bars — if you count the American Legion bar — and one grocery store. At the checkout counter you’ll see a club member, a waiter, and a grounds crewman in line together, all making casual conversation.”

The need for caddies is based on the course’s extreme walkability. After finishing a hole, you stroll directly to the next tee, steps away. The flow of the round is never interrupted, except by the beckoning views. Pioppi, as a caddie, would encourage first-time players to “put their scorecards away and just settle into the experience.” At the completion of a hole, he might keep his foursome at the green and have them try chips and putts from various locations to fully appreciate the course’s design subtleties and unique challenges.

Part of what’s magical about flying to Fishers is the 36-hole factor. Not that someone arriving and leaving by ferry couldn’t go around twice in one day, but it’s much easier to make that happen when you’ve got air travel going for you. One Connecticut PGA professional, so thankful for his invitations to play the course that he asked to speak anonymously, has a plane-owning, golf-loving friend with whom he’s made the hop to Fishers more than once.

“We go wheels-up around 7 a.m., get on the tee by 8:15, play the course twice and we’re back home for dinner,” he says. “Meanwhile, you feel like you’ve gone back in time when you’re there. Nothing ever changes. There’s tremendous wealth, but the property owners consider the island just perfect the way it is.”


Lest you’re concerned that Fishers Island Club is a golf mecca you’re not destined to visit, there are several charity tournaments open to off-island golfers who wish to support a good cause (while checking off a major bucket-list item). In the springtime there’s a fundraiser outing for the Eugene O’Neill Theater Center in Groton, Connecticut, which is across the Sound from Fishers. Also in the spring, the club hosts an event to benefit Fishers Island churches. This year on September 16, it’s the Next Step Fishers Island Charity Golf Tournament, supporting skill development of young people with serious illnesses. Scouting online, you’ll find rounds of golf at the club included in silent auctions by one charity or another.

Of course, if you do happen to have a friend who’s a member, you’ll be playing for your own good cause: Sublime enjoyment of oceanside golf at its absolute finest.


Tradewind offers private charter flights to Fishers Island year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

All photos courtesy of Anthony Pioppi.