Best Weekend Trips to Take in New England This Fall

One of the most beautiful seaside towns in Connecticut, Guilford is a historic 17th-century village with a large town square and the oldest stone house in the country, the Henry Whitfield House. Downtown is full of family-owned shops, and the colonial homes are worth a stroll through the streets. Visit during the Guilford Performing Arts Festival from September 26-29, and catch any number of the 70 acts that will take place in 12 venues, mostly in walking distance of downtown.

Kent, Connecticut, is known for having some of the best foliage in New England, so visiting during autumn is bound to be gorgeous. Downtown Kent features a walkable selection of cafes, antique shops and boutiques, and Kent Falls State Park boasts at least 17 waterfalls, many of which are only a short hike from your car. Bargain hunters should check out the Elephant’s Trunk Country Flea Market — the largest weekly flea market in New England — to poke around at over 500 vendor booths.

The seaside village of Boothbay Harbor is the perfect place for a weekend getaway in Maine. Whether you hop on a boat tour of the harbor or rent a kayak and explore it on your own, you can get up close to islands, lighthouses, puffins, and lobster boats. Downtown you can wander through art galleries, shops, and restaurants, and walk across the longest wooden footbridge in the country. Local highlights are the Coastal Maine Botanical Gardens and the Boothbay Railway Village, which hosts an Annual Fall Foliage Festival on Indigenous People’s Day Weekend. From October 13-15, the festival features artisanal products and food vendors, live music, pumpkin carving, and antique cars.

For a quiet getaway in the northern wilderness, head to Maine’s Rangeley Lakes Region. There are 112 lakes and ponds in the area, with six large lakes to fish, kayak, and canoe in. Moose sightings are common in Rangeley, and brook trout draw fly fishers from all over New England. For those who prefer not to camp out, Rangeley Village offers inns, bed and breakfasts, and rustic lodging, as well as shops and down to earth eateries. In addition to the peaceful waters, enjoy the backdrop of 4,000-foot high mountains.

There are country fairs, and then there’s the Common Ground Country Fair in Unity, Maine. From livestock demos to live musical entertainment to dozens of food vendors, this fair has most of what you’d expect at a country fair but what makes it one of the best agricultural fairs in New England is the variety of workshops. From 9 a.m. September 20 to 4pm the 22nd, there are hundreds of classes and demonstrations on topics such as herbal medicine making, beekeeping, permaculture, composting, and blacksmithing. Don’t get lost in the maze of local farm and artisan vendors, and be sure to catch at least one of the three keynotes.

Along the Mohawk Trail, one of the nation’s first auto-touring roads, lies North Adams, a small town with a burgeoning arts scene since the opening of the Massachusetts Museum of Contemporary Art in 1999. While the museum is a must-see, other attractions include the harmonic bridge, an art installation comprised of resonating tubes under a highway overpass that create music from sounds of passing cars, and the Natural Bridge State Park, a natural archway of white marble that lies in an abandoned white marble quarry. Nearby, hikers and mountain bikers can explore Mount Greylock, the tallest mountain in Massachusetts.

Home of the Norman Rockwell Museum and the Red Lion Inn, one of the country’s oldest continually operating inns, Stockbridge is a small village in the Berkshires with big charm. The town features multiple historic sites and museums to visit, as well as the Hancock Shaker Village, and the Berkshire Botanical Garden. Visit on October 12-13 and attend the 85th Annual Harvest Festival hosted by the Botanical Garden. The festival offers activities for the whole family, including pony and hay rides, classes, live music, over 100 local artisan and farm vendors, and a popular tag sale.

While autumn may seem like a strange time to visit the beach haven known as Cape Cod, the smaller crowds, decreased traffic, and cooler temperatures make fall an excellent time to explore the Cape. Seafood aficionados should attend the Wellfleet OysterFest on October 19 and 20 to taste the local delicacies and brews, and enjoy live music, games, and art. Right on the Cape Cod National Seashore, Wellfleet is a great central location from which to explore beaches and even see live theater performances at the Wellfleet Harbor Actors Theatre.

Mount Washington is the highest peak in the northeastern United States at 6,288 feet, and the historic Mount Washington Cog Railway is the best way to summit the mountain. The train ride is three hours round trip and traverses the steepest railroad tracks in North America, bringing you through multiple climate zones and up to a fantastic view that stretches to the Atlantic Ocean, Quebec, and New York state on a clear day. Nearby Bretton Woods offers resort lodging, restaurants, and numerous opportunities for outdoor adventures, including rock climbing, mountain biking, and hiking. For a family-friendly hike with a massive payoff, head to the Arethusa Falls Trail and visit a nearly 200-foot high waterfall.

Franconia Notch State Park is an outdoor destination that will keep you coming back for years. Drive the scenic parkway and stop at the Flume Gorge, an 800 foot long, 90-foot deep granite crevice full of waterfalls and glacial boulders, or canoe on Echo Lake. Take an aerial tramway ride to the top of Cannon Mountain, or gaze into the Basin, a 30-foot wide pothole in the Pemigewasset River. During the weekend of September 20-22, visitors can head to nearby Lincoln for the annual Highland Games and Festival, a celebration of Scottish heritage, and witness athletic competitions including a stone carry and a hammer throw, traditional music performances, and a sheepdog competition.

New Hampshire is known for its lakes, and Meredith is in the heart of the lakes region, on Lake Winnipesaukee. In addition to its gorgeous natural setting, Meredith boasts numerous historic sites, art and antique shops, and an array of dining options, from cheap eats to upscale restaurants. To really get a sense of the area, drive the length of the Lakes Region tour, a 97 mile driving route that brings you past many of the area’s waterfronts, villages, and mountains, with plenty of places to stop and picnic along the way.

The seaside town of Portsmouth is a bustling New England gem, with a vibrant, walkable downtown. Restaurants, boutiques, and colonial architecture, along with parks and waterfront views, make this city a great place to explore for the weekend. Take a boat tour of the harbor to see lighthouses, the old port, and multiple forts, or visit the Strawbery Banke Museum for living history exhibits. Fans of vintage, antique, and artisan wares will have just enjoyed the Sage Farm Antiques Junque Jam, a market of 100 vendors at Cisco Brewery that offers food and live music, which was held the weekend of September 20-22.

Famous for its seaside beauty and historic mansions, Newport is a destination full of autumn events and activities. While one could spend all weekend taking in the architecture and nature, don’t miss a foray to Escobar’s Highland Farm Corn Maze or a Rail Explorers pedal-powered railway ride. Plan your trip around the Norman Bird Sanctuary Harvest Fair from October 5-6, The Bowen’s Wharf Seafood Festival from October 19-20, or Newport Vineyard’s Harvest Festival from October 26-27.

What isn’t to love about Providence? From Waterfire, a periodic art installation comprised of bonfires, boats, and haunting music along the downtown rivers, to the Brooklyn-esque Providence Flea Market to the Rhode Island School of Design’s museum, this capital city is a bohemian’s dream. See an independent film while seated in a leather sofa with beer in hand at the Cable Car Cinema, take advantage of the plethora of fine dining options, and dance in the streets during PRONK!, a street festival of brass marching bands that takes over South Water Street on Oct 14 from 2-10pm.

Vermont’s Northeast Kingdom is a tri-county area close to the Canadian border that is known for its small towns, dozens of quiet lakes, quintessential country stores and, surprisingly, its artisan food and drink producers. Stay at the Highland Lodge Bed and Breakfast on Caspian Lake in Greensboro, home to Jasper Hill Farm’s award-winning cheese-makers, Vermont-famous Willey’s Store, and the Hill Farmstead brewery, named best brewery in the world for many years by RateBeer.com. Take a hike up Barr Hill or for a scenic drive, head to Lake Willoughby, a glacial lake nearly 5 miles long, that sits between two towering mountains.

Autumn is the season for apple-picking, and the lakeside town of Shelburne is the place to do it. Shelburne Orchards is a 60-acre family farm where you can pick your own apples throughout September and October. Cider donuts and fresh-pressed apple cider are available in the orchard store. Nearby Shelburne Farms sells their own artisan cheeses and pasture-raised meats, and also serves fresh farm-grown foods at their Inn and Restaurant. Just down the road are Shelburne Vineyard and the Shelburne Museum, which houses an array of art, artifacts of Americana, and architecture including a lighthouse and steamboat.