As thermostats dip to comfortable autumn temperatures and nostalgic scents of bonfires fill the air, there’s no better time than the turn of the season to embark on a colorful fall getaway. The Northeast, with its charming small towns and stunning autumn colors, boasts the best places for fall foliage.
Tradewind Aviation offers private charters to vacation spots across the region, bringing you directly to your destination and leaving you more time to relax and make memories with your loved ones. So, grab your coziest sweaters and scarves and get ready for a weekend of fall adventure at one of these three leaf peeping destinations for 2021.
Woodstock, Vermont
Photo courtesy Woodstock Inn & Resort.
Though not as famous as its New York counterpart, Woodstock, Vermont is a storybook small town and one of the best places for fall foliage. As the weather cools, the town comes alive with brilliant red, orange, and yellow hues.
Families should reserve a stay at Woodstock Inn & Resort, a historic property established as an inn by Laurance and Mary Rockefeller. This classic hideaway is the town’s crown jewel and an easy walk to downtown Woodstock’s shops and restaurants. Nearby, couples can reserve their stay at Twin Farms, the storied all-inclusive Relais & Châteaux resort known for its culinary program (it’s adults-only).
For meals, the can’t-miss Mangalitsa is an intimate dinner spot hyper-focused on foods produced locally, and Worthy Kitchen’s burgers and craft beer menu make this casual, locally beloved joint a perfect lunch stop. Guests visiting the Woodstock Inn in September should not miss the Red Barn Dinner Series, a dinner-party style farm-to-table experience held in the hotel’s culinary studio on Thursdays and Sundays throughout the month.
Activities abound in Woodstock during the fall months. Hikers will enjoy summiting Mount Peg, Mount Tom, and the Suicide Six Ski Area for expansive views of the area’s foliage. Or, take in the leaves from the area’s rivers and streams with a private fly-fishing excursion. Should your visit fall over the weekend of October 9-10, head to Billings Farm & Museum for its annual Harvest Celebration, which features 19th century autumn activities such as cider-pressing, bean-shelling, and barn-dancing.
Skip the traditional souvenirs and instead make a stop at Farmhouse Pottery on your way out of town to pick out some locally made ceramic homegoods to commemorate your trip.
Recommended airport: Lebanon, New Hampshire (LEB/KLEB)
Lexington, Massachusetts
The Culinary Garden at Inn at Hastings Park. Photo Courtesy Chip Riegel Photography.
Where better to take in a beautiful Northeast fall than in the birthplace of the American Revolution? Just 15 miles outside Boston, historic and walkable Lexington, Massachusetts is an ideal spot for a weekend of leaf peeping and learning.
The luxurious and charming Inn at Hastings Park is just a five-minute walk from Lexington Common, the battle green where the first shot of the Revolutionary War was fired, and it should be your home base for a weekend of historic exploration. Owner Trisha Pérez Kennealy’s first foray into hospitality, the Inn comprises 22 rooms and suites across three historic buildings. Book a stay in one of the Barn Suites for patriotic yet tasteful red, white, and blue decor. A Relais & Châteaux property, the Inn’s culinary offerings are not to be missed. Town Meeting Bistro offers lunch, dinner, and Sunday brunch, and if you happen to be traveling to the Inn when one of its popular Farm + Vine dinners is happening, be sure to reserve a seat.
Lexington’s walkable town center is awash with color during the fall, but to truly take in the foliage, plan to spend an afternoon driving from Lexington to Concord, Massachusetts. Along the way, stop at historic sites such as the spot where Paul Revere was captured by British forces after his famous midnight ride. Closer to Concord, bibliophiles will enjoy a visit to Louisa May Alcott’s Orchard House, where she wrote and set Little Women. Break for lunch at Main Streets Market & Cafe in historic downtown Concord (try the clam chowder or house ale mac and cheese).
Post-lunch, continue the literary tour with a stop at Walden Pond, the famed stomping grounds of Henry David Thoreau and Ralph Waldo Emerson. Though the pond and surrounding forests are beautiful year-round, they’re particularly breathtaking when fall foliage is out in full force.
Recommended airport: Bedford, Massachusetts (BED/KBED)
Kennebunkport, Maine
The early fall foliage begins to peak through in Maine. Photo courtesy Cliff House Maine.
Maine’s seacoast has historically been most popular in the summer, but autumn is just as beautiful — and often less crowded, making it one of the best places for fall foliage. The turning of the colors typically peaks around mid-October, but the majority of the fall season brings fiery hues that contrast perfectly with the blue sky and ocean. Most businesses stay open through the end of October before taking a winter break.
The charming towns of Maine’s southern coast are all close enough to each other to explore in one long weekend. Cliff House Maine near artsy Ogunquit is perfect for families and group getaways. Set on 70 acres of coastline overlooking the Atlantic, the 226-room resort has plenty of walking trails and activities to keep little ones occupied. For couples, the secluded and romantic cottages at Hidden Pond are the perfect setting for a fall retreat. Even those not staying at the hotel will want to make a special trip to Earth at Hidden Pond, its “farm-to-fork” eatery, for coastal Maine seasonal specialties.
A colorful spread at Earth, a farm-to-fork eatery in Maine. Photo courtesy Hidden Pond.
In Ogunquit, strolling down Marginal Way is the perfect way to take in the foliage and water views. Enter the trail in town, then take it all the way down to Perkins Cove for lunch at Footbridge Lobster, which serves what’s arguably the best lobster roll in town. Nearby Barnacle Billy’s is the perfect happy hour spot (try the rum punch). For entertainment, don’t miss the world premiere of Mystic Pizza on stage at Ogunquit Playhouse in September or Young Frankenstein in October.
Be sure to leave time to explore the villages of Kennebunkport and Kennebunk: Popping into the shops in each town could easily occupy a few hours of your day. If the weather is nice enough to get on the water, consider renting a kayak or canoe or booking a sail on a schooner to explore the area by sea.
Finally, fall festivals are popular in the area: Make sure to stop by York Harvestfest on October 16th and OgunquitFest during October 22-24 for harvest- and fall-themed activities and vendors should your visit coincide with either event.
Recommended airport: Sanford, Maine (SFM) or Portland, Maine (PWM/KPWM)
To learn more about Tradewind’s private charter flights across the Northeast and booking your vacation, please visit our website. To receive a private charter quote, please complete our charter request form or contact our specialists at charter@flytradewind.com or 1-800-376-7922. To learn more about Tradewind’s comprehensive safety plan, please visit our COVID-19 Response page. For the latest travel updates, please visit our Travel Advisory page.