Top 8 Fall Activities in Boston & the South Shore (2026 Guide)
Updated: 38 minutes ago
By: Amanda George, George Group Boston, powered by Lamacchia Realty | Top 8 Fall Activities in Boston & the South Shore (2026 Guide)
There is nothing quite like fall in New England, and this year the calendar across Boston and the South Shore is packed with the kind of local, low-key fun that makes these neighborhoods so special. Whether you're apple picking with the kids, walking the trails with a coffee in hand, or cheering on rowers along the Charles, these are the best fall activities in Greater Boston & South Shore has to offer in 2026. Here are my top 8 picks, from Randolph and Quincy to Roslindale and beyond.
1. Apple Picking at Belkin Family Lookout Farm
Belkin Family Lookout Farm in South Natick is one of the best apple picking spots within easy driving distance of Boston, Dedham, and Needham. The 160-acre orchard grows 29 varieties of apples along with peaches, plums, and pumpkins, and the U-Pick season is in full swing right now.
Where: 89 Pleasant St, South Natick, MA
When: U-Pick open Tuesday through Sunday, 10am to last entrance around 4-4:45pm
Good to know: Purchase U-Pick admission in advance online for a discount
2. Pumpkin Picking at Nihtila Farm
For a true South Shore pumpkin patch experience, Nihtila Farm in Holbrook is a family favorite just minutes from Randolph, Brockton, and Stoughton. It is a classic pick-your-own patch with farm animals, a playground, hayrides, and apple cider donuts on weekends.
Where: 12 Nihtila Ln, Holbrook, MA
When: Fridays, Saturdays, Sundays, and Columbus Day, 10am to 6pm, through the end of October
Good to know: Cash only, with an ATM on site
3. Weir River Farm Fall Festival in Hingham
The Trustees of Reservations host their annual Fall Festival at Weir River Farm on Saturday, September 26. Expect farm animals, tractor rides, craft-making, festival games, live music, and local artisan vendors on the working farm's beautiful grounds.
Where: 140 Turkey Hill Ln, Hingham, MA
When: Saturday, September 26, 11am to 5pm
Good to know: A great half-day outing for families in Weymouth, Hanover, and Norwell alike
4. Weymouth's Great Pumpkin Give-a-Wey
This is a true only-in-Weymouth tradition. The Great Pumpkin Give-a-Wey brings the community together with a pie eating contest, a chowder contest, live music, horse-drawn hayrides, pony rides, and a farmers market, typically held during the first week of October at Weymouth High School.
Where: Weymouth High School, 1 Wildcat Way, South Weymouth
When: Usually the first week of October
Good to know: Free and open to the whole family
5. Fall Foliage Walks at Blue Hills Reservation
Few spots capture New England fall like the Blue Hills Reservation, which stretches across Milton, Quincy, Canton, and Randolph. With more than 125 miles of trails and the Eliot Tower lookout at the summit of Great Blue Hill, it's one of the most accessible places for real foliage views without leaving the South Shore.
Trailheads: Trailheads and parking are available from Milton, Quincy, and Canton sides
Eliot Tower: Offers panoramic views of the Boston skyline and harbor once you reach the summit
Peak foliage: Typically runs mid-October into early November
6. Open Streets Roslindale
Boston's Open Streets series closes out the season in Roslindale on Sunday, October 18. The neighborhood's main corridor goes car-free for a day of local food, live music, small businesses, and community energy, a great way to experience one of Boston's most walkable neighborhoods.
Where: Roslindale Village
When: Sunday, October 18
Good to know: Free and family-friendly, with West Roxbury and Jamaica Plain just a short walk away
7. Head of the Charles Regatta
One of Boston's signature fall weekends, the Head of the Charles brings more than 400,000 spectators to the banks of the Charles River for the world's largest two-day rowing event. It's free to watch from the riverbanks in Cambridge and along the Boston side, with food, vendors, and a genuine fall-in-New-England atmosphere.
When: October 18-19, 2026
Where: Along the Charles River, Boston and Cambridge
Cost: Free to spectate
8. Halloween at Boston Public Market
Boston Public Market wraps up the season with Halloween festivities on Saturday, October 31, featuring family activities, treats from local vendors, and a fun, indoor option if the weather turns. It's an easy stop if you're already downtown or coming in from East Boston, South Boston, or Dorchester.
Where: Boston Public Market, 100 Hanover St, Boston
When: Saturday, October 31
Good to know: Indoor venue, so it's a good backup plan for a rainy fall weekend
(BONUS EVENT) Randolph's Harvest Hoopla!
The Randolph's Inter-generational Community Center puts on an amazing Harvest Hoopla every year in October. Food trucks, giant jumpies, pony rides, face painting, balloon art, petting zoo live music and more! There is usually a fun run and a pet costume parade- this one is amazing for kids, adults, and pets alike.
Where: Powers Farm, 592 N. Main Street, Randolph
When: Saturday, October 17th from 12-4
Cost: Parking and the event are free, with paid mini-events inside
Final Thoughts
Fall is my favorite time to be out in these neighborhoods, whether I'm showing a home in Milton on a crisp Saturday morning or grabbing cider donuts on the way to a closing. My Top 8 Fall Activities in Boston & the South Shore (2026 Guide) barely scratches the surface of what Boston and the South Shore have to offer this season, but they're a great place to start building your fall calendar. If you're thinking about buying, selling, or just want to talk about what a neighborhood like Quincy, Braintree, or Roslindale actually feels like to live in day to day, I'm Amanda George, and I'm always happy to help.
📞 Buying or selling in Boston or the South Shore this fall?
Let's connect: georgegroupboston@gmail.com | www.georgegroupboston.com
George Group Boston, powered by Lamacchia Realty
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