Celebrating a Tradition of Cranberries on Nantucket

Celebrating a Tradition of Cranberries on Nantucket

Think Nantucket, and, most likely, images of windswept seascapes, gray shingled cottages, historic lighthouses, and quintessential New England sailboats come to mind. But the very Cape Cod island people tend to associate with all things maritime also has some interesting agricultural history. It’s home to the once-largest contiguous cranberry bog in the world, and now the largest certified organic cranberry farm in the United States. 

Here, we delve into Nantucket’s cranberry-harvesting past and present, plus an inside look at the ultimate way to immerse yourself in the Ocean Spray world: the Nantucket Cranberry Festival on Saturday, October 12th.

Once Upon a Nantucket Cranberry Bog

Native to the northern latitudes of North America, cranberry shrubs were first cultivated in the early 1800s in none other than Cape Cod, in the blink-and-you’ll-miss-it town of Denis. Centuries prior, the tart red berries had been used for food and dye by Native Americans and the Pilgrims. By the 19th century, cranberries had become quite the delicacy for use in sauces and desserts, and a fledgling Massachusetts housed idyllic wetlands for growing this now-trendy superfood.

Nantucket jumped on the cranberry farming bandwagon in 1857 with the formation of the Milestone Bog in the center of the island. Many more bogs followed, but it was Milestone that soon made history as the largest contiguous cranberry bog on the planet, measuring at a whopping 234 acres.  

As cultivation and irrigation techniques improved, Nantucket farmers figured out that bigger isn’t always better. Once ripe, the berries are harvested by flooding the sunken agricultural lands and allowing the berries to float to the water’s surface. Dividing larger bogs into smaller parcels proved far more efficient for collecting the so-called “red rubies.” With this in mind, Nantucket developed dozens of smaller bogs, and soon cranberry production proved a strong contributor to the island’s growing economy.  

Nantucket’s Present Day Cran-Culture

In the second half of the 20th century, little Nantucket’s cranberry industry became no match for the commercial production that had emerged in Wisconsin, Quebec, and mainland Massachusetts. In August 2019, it was announced that one of the island’s two remaining cranberry operations, the 37-acre Windswept Cranberry Bog, would cease production and transition back into a natural inland wetland — leaving Milestone as Nantucket’s last bog standing. 

Thankfully, under the watchful eye (and ownership) of the Nantucket Conservation Foundation, Milestone’s current 195-acre, 24-bog cranberry excess (and the two million pounds of berries produced there) is here to stay. To ensure this, Milestone has set itself apart from its commercial competitors by becoming exclusively organic, branding Nantucket Conservation Foundation the largest certified organic cranberry grower in the United States. Additionally, in 2004, the Foundation began an annual, one-day Cranberry Festival to raise awareness about Nantucket’s agricultural heritage. Fast-forward to present day, and this adorable festival, which takes place each year over Columbus Day weekend, is one of the most anticipated events of the fall season.

The 16th Annual Cranberry Festival

The 16th annual Cranberry Festival will be held at Milestone Bog on Saturday, October 12th, 2019, from 11am to 4pm. This dynamic affair takes place at the height of harvest season, meaning the land will be glowing with abundant picture-perfect red rubies. It also means that you can strap on a pair of rubber waders, grab a rake and wade through a bog—just like the guys in the Ocean Spray ads. Visitors can either partake in the harvest by raking the berries on the surface, or simply go in a for a few fun pictures.

But, of course, there’s so much more to this festival than a great Instagram post. Guests can feast on amazing cranberry dishes from local vendors, such as the cranberry pecan bread from Wicked Island Bakery, cranberry pies from Bartlett’s Farm, cranberry fudge from Aunt Leah’s Fudge, and fresh-pressed juice from ACK Fresh. There are also opportunities to learn about traditional versus organic techniques from professional farmers through one-on-one discussions and guided tours. Plus, you can check out the operational, antique berry bouncing machine (as it sifts berries) and browse a very cool collection of antique tractors.  

Children are sure to love the hayrides along the bog as well as other kid-friendly happenings, including a petting zoo, face-painting, sack races, and meet-and-greets with some of the fluffy sheep living at Milestone (who are supervised by the resident Border Collie, Rem). Meanwhile, adults will appreciate the live music, you-pick areas (for taking a few pounds of the good stuff home), harvesting demos, and self-guided walking trails through the bog and surrounding autumn scenery. This off-the-wall themed festival is a great way to immerse yourself in all things cranberries — with the exception of a vodka cranberry cocktail in hand.


Tradewind offers regularly scheduled shuttle flights to Nantucket from late April through early December, as well as private charters year-round.

Featured Photo: J. Greg Hinson

The Culinary Outposts of Northern Vermont

The Culinary Outposts of Northern Vermont

A featured story by David Gould, a renowned travel writer and former Executive Editor of Travel + Leisure Golf.


You can stroll into most gourmet shops these days and purchase Himalayan pink salt blocks, mined in Pakistan from deposits more than 100 million years old. But in the late 1990s, when I was introduced to these epicurean wonders, they weren’t so well-known.  

The setting was a chef’s-kitchen dinner for a small group of food critics and travel writers in northern Vermont. Our host hand-grated some of his ultra-pure salt crystal for us, as the food critics smiled discreetly. From that night forward, I was aware that traveling due north in the Green Mountain State didn’t mean you were leaving civilization behind — not hardly.

Northern Vermont is something of an epicurean hotspot, with three main towns holding court as its culinary centers: Stowe, Burlington, and Middlebury (and their surrounding areas). Explore the best of each on a three-stop itinerary via Tradewind Aviation.

Fly into Stowe on a private charter or shuttle flight (resuming in December), and you’ll soon find yourself on a descent into Morrisville–Stowe State Airport, staring at the giant’s-face-in-profile view of Mt. Mansfield’s 4,300-foot peak, complete with its forehead, nose, lips and chin. May sound corny, but if you hike up there it’s likely you will use those features to navigate. 

Also out the aircraft window should be glimpses of Montreal, just 100 miles to the north and a steady source of prosperous, urbane tourists who know fine dining when they come upon it. Their influence, combined with the luxury vacation-home culture generated by Stowe and other ski resorts, generates considerable demand for cool things to see, do, and dine upon.

Photo: Plate

Photo: Plate

In the village of Stowe and down Route 100 at the eponymous resort, there’s no shortage of options for where to dine. Inside six-year-old Plate, on the village’s Main Street, you’ll find locals and visitors alike in comfortable booths of slate gray with polished wood trim under sparkly pendant lighting. The menu, atmosphere, and execution all adhere to lofty standards at Plate — presentation of the dishes is artistic, though never precious. There are small plates for the foodie who wants to sample and savor, but also generous portions of Curry Pork Loin or Jamaican Jerk Half Chicken, if you’re up for it. Reservations are suggested. 

The decor and branding of highly popular Doc Ponds may seem reminiscent of legendary local jam band Phish and the creative-slacker element found in any prominent ski town. But then you’ll consider how much discipline and devotion it takes to make an ambitious restaurant concept succeed the way this one has. A scan of the Doc Ponds menu shows comfort recipes wherever you look, but visually and gastronomically it’s a refined experience (don’t be surprised if post-graduate discussions of beer and how it’s produced arise).

Even during a tour of northern Vermont is by plane, the gondola ride up to the Cliff House Restaurant at Stowe Mountain Resort should still be a kick, and the wall of windows inside this chalet-style eatery offer breathtaking views of inspiring panoramas. Logically enough, the restaurant serves lunch only, except for the dinner opportunities afforded via a special Summit Series schedule of themed evenings.

Photo: Stowe Mountain Resort

Photo: Stowe Mountain Resort

A quick Tradewind flight over to Burlington International Airport is next, transferring you from an alpine backdrop to an urban one. As you approach the Champlain waterway, you’ll get a chance to discover, as I have, that the prairie-like parts of the state are as visually poignant as the mountainous regions.

It was here in greater Burlington, by the way, that I received my introduction to the dazzling pink salt block. That evening’s intimate dinner was hosted by a first-class hostelry now known as The Essex, Vermont's Culinary Resort & Spa. Conditions are right to make Burlington an outpost of the so-called “culinary vacation business,” and the location of The Essex next door to the prestigious New England Culinary Institute is emblematic of the collaborative energy that keeps the local foodie scene humming.

Hotel Vermont, with its plain-country name contradicting its chic sophistication, is an obvious choice for lodgings. The hotel’s bar and restaurant, Juniper, is visually appealing with its copper, hardwood, and gleaming glassware. There’s even an outdoor space with a fire pit and Adirondack chairs. Order the Lake Champlain Perch with frisée, malt vinegar, shallots and hazelnut oil. In the same neighborhood are two other top-rated Burlington restaurants, Hen of the Wood and Bleu Northeast Seafood. These three award-winners are mainstays of what’s considered the Cherry Street dining scene, and empty tables are rarely spotted up and down the boulevard.

Photo: Marshall Webb

Photo: Marshall Webb

The Inn at Shelburne Farms, the centerpiece of a 1,400-acre preserve along Lake Champlain, is a destination all its own. You get here from Burlington via Route 7 on a ride that is quite short, especially given that it takes you back in time a century or two. To enjoy dinner here you have to make reservations a month in advance. The rooms are exquisite, but the place has no central heating or air conditioning. Cuisine doesn’t get any more farm-to-table than the ISF, but if you simply want the vibe of the place, wander by to watch the artisan cheesemaking operation. It’s housed in a cathedral-like barn and produces cheddar that’s almost too good to share with your house guests, every block of it made from raw milk produced by the Brown Swiss cows that roam the acreage in country contentment. 

The third stop on your tour brings you into Middlebury State Airport, a few miles southeast of the the town’s central business district. Part college town, part county seat, Middlebury is an easy place to feel comfortable in as soon as you arrive — all the more so if you drop by the spirited Two Brothers Tavern on Main Street. You can try their cheddar ale soup, grilled Spanish octopus or the popular comeback burger, made with comeback sauce and offering a taste of Southern-style cooking in the north country. Sabai Sabai Thai Cuisine is a can’t-miss stop for high-quality Asian food — it’s known for a squid specialty called khan soi

Drive 15 minutes up Route 7 and you'll come upon the little city of Vergennes, named for a French nobleman who helped swing the American Revolution our way. On Green Street you’ll find Bar Antidote and its pub-crawl pairing, Hired Hand Brewing. The location is hard to miss, given the retro, better-living-through-chemistry logos of these two establishments.

We’ve known for quite a while that this part of Vermont attracts chefs and innkeepers who could be working in the big cities, but come here instead for the lifestyle. But interestingly, a Vermont farm kid, Ian Huizenga, is currently outdoing most (if not all) of those who parachuted in. Huizenga is the chef and brewer behind Antidote and Hired Hand. He was named Vermont Chef of the Year in 2017, but his talents extend beyond cooking and beer-crafting to interior design and the artistry that goes into his branding and graphics.

Hired Hand would be part of the farm-to-glass movement, if there were enough microbreweries using local ingredients to actually call it a movement. The sourcing effort Huizenga makes to hyper-localize his product is tireless, but worth it. Downstairs from the brewpub, Bar Antidote is where locals and visitors gather to dine on grilled Vermont flat iron steak served on roasted mushroom toast and crispy-crust pizzas — also made with locally sourced fixings.  

If you find that you keep extending your visit, be advised that people have become residents of this region very gradually — without ever consciously deciding they would move here. 


Tradewind will offer shuttle flights to Stowe beginning in December 2019, and also offers charter flights to Stowe, Burlington, and Middlebury year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured photo: Mark Vandenberg

Five Must-See Lighthouses of Nantucket and Martha’s Vineyard

Five Must-See Lighthouses of Nantucket and Martha’s Vineyard

Throughout the 18th and 19th century, a heady mix of unforgiving seas, craggy ocean shallows, and shifting sand banks branded the waters off Cape Cod a shipwreck hotspot. In response, lighthouses were strategically built across the Nantucket and Martha’s Vineyard to protect both sailors and the isles’ burgeoning seafaring-related industries.  

Today, the well-preserved, high-rising structures collectively shine a light—pun intended—on the history and development of these two islands. While these lighthouses are no longer critical thanks to technological advancements in maritime navigation, many remain automated workhorses.

More importantly for travelers, each makes for incredible photographic opportunities and excites the imagination with stories of yore. Here, we present five iconic, must-see lighthouses blending the past with the present on Nantucket and Martha’s Vineyard.

Brant Point Light, Nantucket

Photo   : Dou Kerr via Flickr / CC BY

Photo: Dou Kerr via Flickr / CC BY

This 26-foot-tall, circa-1901 lighthouse is officially the shortest lighthouse in all New England. But there’s no Napoleon complex here: Given its proximity to Nantucket Harbor, this all-white wooden beauty is arguably the most photographed site on the island. And thanks to its near three-century past, it’s a big-deal entry on the National Register of Historic Places.

The current structure is the tenth—yes, tenth—rebuild of the second-oldest lighthouse in the country (originally built in 1746, prior to the formation of the United States of America itself). It was automated in 1965, and today, it still beams its bright red light up to ten nautical miles.

Edgartown Harbor Light, Martha’s Vineyard

Photo   : Rfgagel via Wikimedia Commons / CC BY

Photo: Rfgagel via Wikimedia Commons / CC BY

Believe it or not, this Edgartown icon, which today marks the entrance to Edgartown Harbor, was slated for demolition as recently as the mid-1980s. Under operation by the United States Coast Guard, the circa-1939 cast-iron landmark had fallen into disrepair. But now, under the stewardship of Martha's Vineyard Museum and Martha's Vineyard Historical Society, the lighthouse shines in full glory.

Tours allow visitors to enter inside and climb up to the lantern room. Be sure to ask the lighthouse keeper of the building’s odd and dramatic history, which traces back to an original incarnation (built in 1828) over in Ipswich.

Gay Head Light, Martha’s Vineyard


Given its prime location in Aquinnah (aka Gay Head) in the southwest reaches of Martha's Vineyard, this lighthouse is best appreciated at sunset. But at any time of day, Gay Head Light offers a glimpse of the old Martha's Vineyard. It was erected as the island’s first lighthouse at the turn of the 18th century, though its current red-brick aesthetic reflects a rebuild in 1844, and its current location is thanks to a meticulously-executed, piece-by-piece move in 2015.

With white and red lights that reach 24 and 20 nautical miles, respectively, the lighthouse still keeps sailors aware of the perilous underwater rocky ledge known as Devil's Bridge, much like it did centuries ago. The lighthouse is open for tours seasonally through the Town of Aquinnah.

Great Point Light, Nantucket

Photo   : Tim Sackton via Flickr / CC BY

Photo: Tim Sackton via Flickr / CC BY

Reaching the so-called “Nantucket Light” is a New Englander’s rite of passage. This fully operational, all-white stone lighthouse, rebuilt in 1986 to reflect its original 1784 appearance, stands at Nantucket’s northernmost point on a small spit of land where the Atlantic Ocean and Nantucket Sound meet.

Tucked deep within the Coskata-Coatue Wildlife Reserve and known for its unspoiled dunes and prolific birdlife, the lighthouse is accessible only by sandy roads. Meaning, you’ll need to walk seven miles on foot, rent a four-wheel-drive vehicle (with the proper beach permit), or pre-plan for a guided-tour with The Trustees of Reservations of Massachusetts. Whichever you choose, expect to reap worthwhile rewards by taking this (unpaved) road less traveled.

Sankaty Head Light, Nantucket

Photo   : Matt P. via Flickr / CC BY

Photo: Matt P. via Flickr / CC BY

Near the easternmost tip of Nantucket in the village of Siasconset, this 70-foot-tall, brick-and-granite lighthouse dates back to 1850, when it was built on a bluff straddling one of Nantucket’s most raw and wild coastlines. Though it was moved 400 feet inland in 1987 as a protection against bluff erosion, the historic lighthouse still operates as a navigational tool today, beaming a white light out 24 nautical miles every 7.5 seconds.

The lighthouse itself is closed to visitors, but the grounds are not. Given its remote location and few visitors, anticipate having this man-made marvel mostly to yourself—and your deep thoughts.


Tradewind offers regularly scheduled shuttle flights to Martha’s Vineyard (May through November) and Nantucket (late April through early December). Tradewind also offers private charters to both Martha’s Vineyard and Nantucket year-round.

Featured Photo: Doug Butchy via Flickr / CC BY

Goodspeed Card Charter Program: A New Way to Fly Private

Goodspeed Card Charter Program: A New Way to Fly Private

Whether frequent fliers use private aviation for business meetings, leisure trips, or the occasional adventure, booking a private charter shouldn’t be complicated. That’s the idea behind Tradewind Aviation’s recently unveiled Goodspeed card charter program — which stands out from conventional private charter services with a simplified pricing solution and significant cost savings.

Free of initiation fees, membership fees, peak day surcharges, and blackout dates, Tradewind’s new pre-purchase flight card offers discounts between 20 and 30 percent over comparable programs, in large part due to the company’s ability to leverage its internal fleet of Pilatus PC-12s. As a direct operator of its flights, Tradewind Aviation has operational efficiencies that it passes along to its customers in the form of cost savings.


“The Pilatus PC-12 is a very efficient aircraft, offering similar performance to a King Air 350 at significantly less operational cost,” says David Zipkin, Vice President of Tradewind Aviation. He adds, “Our mission is to provide the safety and quality of service that is normally found only on larger jets for a fraction of the cost. The Pilatus PC-12 is a proven performer on short and medium range flights and we’re thrilled to offer the largest fleet of on-demand PC-12s in North America.”

While charter pricing is usually calculated based on the total flight time required to accomplish a trip (including plane repositioning and empty legs), Tradewind’s occupied rate program bases the cost solely on the flight time of a client’s trip. According to Zipkin, the response since the flight card’s launch has been exceedingly positive.


“We have always offered a very attractive charter product, but traditional pricing can be difficult to understand and the effective hourly rate can vary from route to route,” he explains. “With the new program, empty legs are included, which offers predictability of pricing and flexibility to fly anywhere in the region for a flat hourly rate.”

As with Tradewind’s other programs, the Goodspeed card conveniently services sought-after regions in the Northeast and the Caribbean, including smaller airports that are only accessible by the versatility of the Pilatus PC-12s, such as the landing strips on Fishers Island, Montauk, and Provincetown.


Available in three tiers to accommodate different flyer needs, the program’s savings begin at only 10 hours of private charter flight time. And with airport and landing fees also included, clients will never be surprised with hidden costs.

The benefits of the Goodspeed card don’t end with Pilatus PC-12 charter flights. Members can also take advantage of 30 percent discounts on day trips, 10 percent discounts on shuttle routes throughout the Northeast and the Caribbean, and 5 percent discounts on charter transfer throughout North America via the company’s fleet of Citation CJ3 jets. Add to that the luxury perks that all Tradewind clients enjoy — such as streamlined security, private gate entrance, exclusive FBO lounges, and complimentary on-board snacks and drinks — and Goodspeed card holders can expect a smooth transfer each and every time they fly.

To learn more about the Goodspeed Card Charter Program, please visit the Tradewind Aviation jet card program page.

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