Fall is a beautiful time of year to visit the Boston area, and there’s no more quintessential fall activity than apple picking! But there’s so many more fall activities in Boston—check out our list below of the top 4 things to do in Boston this fall that go beyond apple picking.

  • Feast for all senses at Nashoba Valley Winery: Located in scenic Bolton, MA (about an hour from downtown Boston), Nashoba Valley is so much more than a winery. There’s a vineyard and tasting room, yes, but also a brewery, restaurant, farm and picnic area all on 50 acres of beautiful countryside. The winery and brewery are open every day of the week and feature numerous areas for outdoor seating, including some areas where you can bring your own food. They host several special events throughout the fall, including an Oktoberfest celebration (tickets required). Plus, if you just can’t stand the thought of fall without apple picking, there’s a pick-your-own orchard right onsite. (Nashoba Valley Winery, 100 Wattaquadock Hill Rd, Bolton, MA)

    Nashoba Valley Winery by Massachusetts Office of Travel and Tourism

  • Take a (leaf-peeping) Hike at Noanet Woodlands: New England is known for its gorgeous autumn leaves, and a hike might just be the best way to enjoy them. 25 miles southwest of Boston, you’ll find Noanet Woodlands’ more than 17 miles of trails and wooded roads. The highlight is a hike to the top of Noanet Peak, which offers views of the Boston skyline rising from the countryside. Trails are open daily, sunrise to sunset, and there is a $5 parking fee. (Noanet Woodlands, Powissett Street, Dover, MA)

    Photo by Mike Halsall

  • Cheer on the Rowers at the Head of the Charles Regatta: Yes, the Head of the Charles is the largest 2-day regatta in the world, bringing more than 11,000 athletes to compete. But the event is more than just boat races—it’s a weekend-long celebration, with thousands of spectators watching the races first-hand from the shore. Food, drinks, and souvenirs are available all along the river, and many boathouses hold open houses for guests to explore. Keep in mind that the area will be quite crowded, so take public transportation or catch one of the free shuttle buses offered by the Regatta. (Head of the Charles Regatta, viewing sites throughout Boston and Cambridge along the Charles River)

    Photo by EandJsFilmCrew

  • Get Spooked at Witches Woods or a Ghosts & Gravestones Tour: October is the month for frights, whether you’re in the city or making a trip out to the burbs. Witches Woods, a “Screampark,” located in Westford, MA, offers a haunted hayride, multiple themed haunted houses (including one in 3D!), and a spectacular display of hundreds of professionally carved jack-o-lanterns. If you’re staying in the city, Ghosts & Gravestones is a trolley tour of Boston’s spookiest sites, including ancient burial grounds and the city’s “most haunted hotel.” Tickets are required for both Witches Woods and Ghosts & Gravestones; check their sites for exact schedules. (Witches Woods, 79 Powers Road, Westford, MA. Ghosts & Gravestones, boarding at 200 Atlantic Avenue, Boston, MA).


    With over 50 hotels in the Greater Boston area, let Hilton help you make a staycation out of your fall exploration and these four great things to do in the fall in Boston.

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