Top Fall Activities in Greater Boston 2025 | Team Picks

Fall in Greater Boston is more than just crisp air and colorful leaves. It is a full season of activities, traditions, and cozy at-home rituals. Whether you are heading out to apple orchards, visiting local festivals, or making cider in your own kitchen, there are plenty of ways to make the most of autumn.

Classic Fall Activities Near Boston

Apple Picking

Apple picking is a New England classic. Our team even has a whole guide to the best apple orchards near Boston. If you want a quick day trip, Lookout Farm in Natick is just 30 minutes from the city. For cider donut lovers, Russell Orchards in Ipswich is a must. These U-pick orchards are also some of the most searched fall activities near Boston.

Pumpkin Patches

No fall is complete without a visit to the pumpkin patch. Families love Shelburne Farm in Stow, which combines pumpkin picking with hayrides and a kid-friendly play area. If you want to pair your pumpkin search with cider donuts, Connors Farm in Danvers delivers the full fall farm experience. These pumpkin patches in Massachusetts are some of the best for families looking for a day trip.

Corn Mazes

Corn mazes are a great way to spend a crisp afternoon outdoors. Connors Farm is known for its elaborate themed maze, while Mike’s Maze in Sunderland is worth the drive for one of the most creative mazes in Massachusetts.

Fall Festivals

Boston’s fall calendar is packed with festivals. In Cambridge, the Harvard Square Oktoberfest and HONK! Parade combines music, food, and beer gardens. Somerville goes sweet with the annual Fluff Festival, celebrating the city’s marshmallow-fluff heritage. For families, the Topsfield Fair is a fall tradition that draws visitors from across Greater Boston.

Leaf-Peeping Hikes

Fall foliage in Massachusetts is unbeatable. For easy access, head to Middlesex Fells Reservation, where trails wind through colorful forests just minutes from Boston. Blue Hills Reservation is another great choice for sweeping views of the skyline surrounded by fall colors. These are two of the most popular spots for leaf-peeping near Boston.

Fall Activities at Home

Pumpkin Carving or Painting

Pick up a few pumpkins from a local farm and host a carving or painting night. It is a fun way to get creative and makes for instant seasonal décor at home. If you want to take it further, set out snacks and make it a party. Check out these Halloween party platter ideas for inspiration.

Fall Recipe Night

Invite friends over and ask everyone to bring a fall recipe they have been wanting to try. You can cook together or simply share dishes around the table. We recommend this Baked 4 Cheese Butternut Squash Rigatoni or this Chai Pumpkin Cake from Half Baked Harvest.

Cozy Home Décor Projects

Make your space feel like fall with simple DIY projects. Try a wreath with seasonal leaves and berries, swap out throw blankets for warmer textures, and light apple cider or pumpkin candles.

Movie Marathon

Turn your living room or backyard into a mini theater. Hang a sheet and set up a projector for a scary movie theme with classics like Halloween and Poltergeist, or keep it cozy with fall favorites like Hocus Pocus and When Harry Met Sally.

Backyard Fire Pit

Gather family or friends around the fire pit for s’mores and hot cider. A few blankets and string lights make it feel extra cozy. Want to surprise your guests? Try these savory s’mores with cheese and herbs for a fun twist.

Fall Activities for Adults

Local Breweries

Seasonal beers are everywhere in fall. Try Night Shift Brewing in Boston or Lord Hobo Brewing in Woburn for special releases. Breweries are one of the top fall activities for adults in Greater Boston.

Wine Tastings

Nashoba Valley Winery in Bolton offers tastings alongside apple picking and has a restaurant on site with seasonal menus.

Haunted Houses and Spooky Tours

Salem Haunted Happenings is one of Massachusetts’ biggest October draws. If you prefer to stay closer to the city, book a Boston Ghost Tour for a spooky night out.

Outdoor Fitness

Cooler temperatures are perfect for exercising outside. Head to the Esplanade in Boston, where outdoor yoga and fitness classes are often held by the river, or take a fall hike at Walden Pond State Reservation to stretch and breathe surrounded by peak foliage.

Craft Fairs and Farmers Markets

Support local vendors at Massachusetts farmers markets, where you can find seasonal produce, fall décor, and artisan crafts.

Final Thoughts

Fall in Greater Boston is packed with options. You can spend a weekend apple picking near Boston, visiting pumpkin patches across Massachusetts, or joining in on fall festivals like the Harvard Square Oktoberfest. Families will love the kid-friendly corn mazes and hayrides, while adults can enjoy breweries, wineries, and haunted tours. And if you prefer staying in, fall activities at home like recipe nights, pumpkin carving, and backyard fire pits bring the season to life without leaving your doorstep. From U-pick orchards to cozy nights in, there is no shortage of things to do in Boston in fall 2025.