Special Report

34 Fall Weekend Trips You Should Plan Now

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1. Woodstock, Vermont

If you’re looking for a quaint village with picturesque scenery, then Woodstock, Vermont is a great fall weekend trip, and a manageable drive from major cities such as Boston and New York. Located on the banks of the Ottauquechee River and among the Green Mountains, Woodstock features the only national park in Vermont, Marsh-Billings-Rockefeller National Historical Park, and three historic covered bridges. Nature lovers can view the changing leaves while hiking, biking, visiting a local farm or wandering around the village. Visitors can stay at the Woodstock Inn & Resort, complete with a spa, golf course, and upscale farm-to-table dining, or one of the area’s many bed and breakfasts. You can also try an array of delicious restaurants in town, including seasonal specialities at Mon Vert Café. Or browse the family-owned shops, including a classic general store, F.H. Gillingham & Sons.

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2. White Mountains, New Hampshire

The White Mountains region of New Hampshire offers many ways to enjoy the fall colors. See what nature has to offer in the comfort of your car via one of the many scenic drives, such as the Kancamagus Scenic Byway through the White Mountain National Forest. Visitors can also take a hop on the Conway Scenic Railroad or a gondola ride to the top of a mountain–and even enjoy a snowless dog sled tour from mid-September to November. There is also Jackson Village, complete with a covered bridge and waterfalls. In October, this village features more than 80 different locations with “Pumpkin People” on display.

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3. Newport, Rhode Island

Summer may seem like the ideal time to visit Newport, Rhode Island, but fall visitors can enjoy many of the same amenities the area has to offer without the crowds–and with lower hotel rates. For a more interesting hotel option, try the Rose Island Lighthouse, where you can stay in the historic lighthouse on an 18-acre island. There are plenty of delicious and upscale dining options, including the White Horse Tavern with its fireside ambience. As America’s oldest tavern, George Washington once stayed here, and the place is rumored to be housed in a haunted Colonial building. If you’re craving more spookiness, try a lantern-led ghost tour. For something more relaxing, there is Newport Vineyards, waterfront shopping, or the state’s only hydrotherapy spa.

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4. Berkshires, Massachusetts

Full of foliage, museums and history, the Berkshire Mountains, located in western Massachusetts, offer plenty to do for the autumn traveler. For a scenic road trip, take a drive up Mount Greylock, the highest peak in Massachusetts. Nature enthusiasts can also hike part of the Appalachian Trail or take a fall foliage train ride. There are several museums for history buffs and art lovers, including the Norman Rockwell Museum. Shopaholics can try browsing independent booksellers and toy shops, or check out an antique dealer in one of the local towns. For more relaxation or a unique experience, try a goat yoga class in October at Hancock Shaker Village.

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5. Martha’s Vineyard, Massachusetts

Beloved by celebrities and politicians, Martha’s Vineyard in fall offers ideal temperatures, fewer people, and a food and wine festival. Located seven miles off Cape Cod, the island’s population balloons from about 15,500 in the off-season to 115,000 in the summer. Fall visitors can take in the beautiful scenery and beaches and shopping and dining options with more breathing room. There are also special events unique to the season, including the Martha’s Vineyard Food & Wine Festival in late October and the Striped Bass & Bluefish Derby fishing tournament running from this Sunday through October 19.