The best Thanksgiving getaways from Boston in New England & beyond

The Berkshires come alive in the Fall. From the foliage to the theater, this is a must for anyone in Boston. Hike along the Appalachian Trail, explore cultural gems like the Clark Art Institute and the Norman Rockwell Museum and savor farm-to-table delights in cozy towns like Lenox and Stockbridge. As the leaves fall, the Berkshires come alive, offering a truly enchanting seasonal experience. The place to stay in the Berkshires is Pittsfield and the Hotel on North is a great choice. This boutique hotel in the heart of downtown offers an industrial chic home away from home. 

Head up to New Hampshire to stay in a Getaway House. Getaway Houses are tiny cabins (about 200 square feet) that are designed for a single person, couple or two friends, and feature queen size beds, a small kitchen with a refrigerator, running water and a bathroom that includes a shower and toilet. In the Boston area, there are several locations that are easy to access by car. Blake Brook, which is in Ec, is a one-and-a-half-hour drive from town. This puts visitors close to Epson Town Forest for hikes and stunning views, and an easy drive to Concord if you’d rather not attempt cooking dinner over a fire. 

Nestled in the Equinox Mountain Valley along the Battenkill River, Hill Farm is a quaint Vermont inn worth visiting this fall or winter. Hill Farm started life as a dairy farm in 1779 and is now a sustainable vegetable farm that invites guests to experience farm-to-table dining in a luxurious, cozy setting. The entire property has been designed to highlight the works of local artisans and there are plenty of opportunities to experience the local culture through a wide range of activities like farm tours, culinary classes, fly-fishing, hiking, natural dyeing and yoga.

Nantucket is amazing all year round, but it is especially magical in the off season. The summer crowds are gone, but the ocean breeze and charming streets are still there. Dine at or, The Whale (38 Main St, 508-825-5897) located right on the cobblestoned main street in downtown Nantucket, if the weather is still nice you can enjoy eating on or The Whale’s back patio. Joining the island’s foodie ranks last summer, Sister Ship at Faraway Nantucket is a shiny beacon on Centre Street also worth booking. The farm-to-table restaurant presents a Mediterranean-influenced menu with all their ingredients sourced from farmers and producers throughout Nantucket.

While some may balk at the idea, a weekend getaway to Europe from Boston is very possible--especially when you have an extra-long weekend! Icelandair is a particularly smart choice in airline when looking at weekend getaways to Europe that won't break the bank. With their hub located in Reykjavik, you can seamlessly connect to numerous European cities without having to face the customs lines in places like Paris or Amsterdam because you will get your passport stamped in Iceland while still getting access to a plethora of destinations. Their competitive pricing and frequent deals make international travel accessible. Additionally, Icelandair's schedules often allow for extended layovers in Iceland itself, adding an extra layer of adventure to your journey. Whether it's a romantic weekend in Paris or a party weekend in London, a European getaway from Boston is both feasible and well worth it!