Fall Things to Do in Greater Boston: Our 2026 Guide to Apple Picking, Festivals & More

Fall in Greater Boston is one of those seasons where there is almost too much going on. Apple picking, cider donuts, neighborhood festivals, foliage walks, Oktoberfests, regattas, pumpkin patches. You could fill almost every weekend from Labor Day through Thanksgiving without trying very hard.

So rather than give you a giant list of every fall activity we could find, I pulled together the places and events our team actually recommends, along with some Greater Boston traditions that are worth putting on the calendar.

Some are annual favorites. Some are places members of our team have actually visited and would recommend. And one, the Arlington EATS Turkey Trot, is especially close to us because the Santana Team is sponsoring it this year. We'll be there with hot coffee and donuts for runners and walkers, which feels like a perfectly reasonable reward for voluntarily running a 5K in November.

2026 Greater Boston Fall Calendar at a Glance

If you're the type of person who plans fall weekends before summer is technically over, here are some of the dates worth saving.

Apparently September 19 is the day Greater Boston collectively decided to schedule fall.

Our Favorite Apple Picking and Pumpkin Spots Near Boston

New Englanders take apple picking seriously.

Some people have an orchard they return to every year. Others choose based on the drive, the crowds, the apple varieties, or whether there is enough happening to keep kids occupied.

And then there are the people who are really just there for cider donuts. I respect their clarity of purpose.

We haven't been to every apple orchard or pumpkin patch in Massachusetts, but our team does have favorites.

Emily's Picks: Shelburne Farm and Russell Orchards

I've been to both Shelburne Farm in Stow and Russell Orchards in Ipswich, and I'd recommend either one depending on what kind of fall day you're looking for.

Shelburne is a great choice west of Boston if you want the classic New England orchard experience without turning apple picking into an all-day road trip. It's only about 20 miles from Boston and has pick-your-own apples and pumpkins, warm cider donuts, hayrides, farm animals and play areas. The farm grows more than 100 apple varieties throughout the season.

Russell Orchards is my North Shore pick, and yes, the cider donuts are absolutely part of the reason. Apple picking generally runs through September and October, and there is also a farm store, animals, picnic area and winery.

For me, Shelburne is the pick for an easy, activity-filled orchard day west of Boston. Russell is perfect if you're heading toward Ipswich and want a quintessential North Shore fall outing, preferably with a warm cider donut involved.

Katrina's Pick: Smolak Farms

Smolak Farms in North Andover has long been Katrina's pick on our team, especially if you want apple picking to turn into more than a quick stop at the orchard.

The farm combines pick-your-own fruit with hayrides, a playground, animals, a farm stand and seasonal festivals. In September and October, its family festival weekends also include apple picking and pumpkin picking.

For the Full Pumpkin Patch and Corn Maze Experience

If your definition of fall requires pumpkins, a corn maze and enough activities to occupy most of a Saturday, Connors Farm in Danvers is one of our picks.

Its 2026 Fall Fun season runs through early November, with a corn maze, hayrides, train rides, play areas and other activities. Fall at the farm also includes apple and pumpkin picking and cider donuts.

For something closer to the city, Belkin Family Lookout Farm in Natick is another easy option for apple picking near Boston, with U-pick fruit and additional seasonal activities.

If apple picking is the main event rather than one stop on your fall calendar, we put together a whole guide to our favorite apple orchards near Boston.

Farm note: Picking conditions, available crops, ticketing and hours can change quickly depending on weather and harvest conditions. Always check the farm's current picking status before heading out.

Fall Festivals We Actually Put on the Calendar

Apple orchards get most of the fall-attention glory, but some of my favorite Greater Boston fall activities happen much closer to home.

Arlington Town Day

Arlington Town Day is one of those events that simply belongs on the local calendar.

On Saturday, September 19, Mass Ave between Pleasant and Jason Streets fills with local organizations, businesses, food and activities from 10:30 a.m. to 4:30 p.m.

If you're newer to Arlington, it's also a particularly good way to see how many businesses, organizations and community resources are packed into one town.

What the Fluff? Festival in Somerville

There are normal fall festivals.

And then there is a festival celebrating Marshmallow Fluff.

What the Fluff? returns to Union Square on September 19 from 1 to 5 p.m. The festival celebrates Somerville's connection to Marshmallow Fluff with food, music, games and the particular brand of weirdness the city handles exceptionally well.

It is hard to imagine a more Somerville event, and I mean that affectionately.

HONK! and Harvard Square Oktoberfest

If you've never experienced HONK!, describing it simply as a festival of activist street bands does not quite prepare you for it.

The 2026 HONK! Festival runs October 9–11 in Somerville, bringing bands, performances and plenty of noise to Davis Square and the surrounding area.

On Sunday, October 11, the celebration continues into Cambridge with the 47th Annual Harvard Square Oktoberfest and 21st HONK! Parade.

This is one of those weekends when walking or taking the T becomes considerably more appealing than attempting the uniquely Greater Boston recreational activity known as finding somewhere to park.

Medford's October Lineup

Medford has several 2026 fall events worth knowing about.

The city's Oktoberfest is October 3 on Riverside Avenue, followed by Harvest Your Energy at Riverbend Park on October 17 and the Pumpkin Float and Lantern Parade at Wright's Pond on October 24. You can check the City of Medford's event information for the latest details.

The Pumpkin Float is the one I'd especially flag if you're looking for a smaller local fall tradition with a little spooky-season energy.

A Few Boston Fall Favorites

People who live in Somerville, Arlington, Cambridge or Medford do, occasionally, cross the river and attend events in Boston. Brave, I know.

These are a few city events I'd actually put on the calendar.

Boston Arts Festival

The Boston Arts Festival returns to Christopher Columbus Waterfront Park on September 12 and 13 from 11 a.m. to 6 p.m.

The free two-day festival showcases Boston-area artists and musicians, with visual art, handmade work and live performances along the waterfront.

This is a particularly nice early-fall Boston day because you can wander the festival, walk along the Harbor and easily turn it into lunch or dinner in the North End.

Boston Local Food Festival

If the cider donuts have already established that food is an important theme of this guide, the Boston Local Food Festival belongs here.

The 2026 festival takes over the Rose Kennedy Greenway on Sunday, September 20 from 11 a.m. to 5 p.m. with local food vendors, demonstrations, activities and food from around New England.

This is one I'd arrive hungry for.

Head of the Charles Regatta

Even if rowing does not normally factor heavily into your weekend plans, the Head of the Charles Regatta is worth experiencing at least once.

The 2026 regatta takes place October 16–18 along the Charles River between Boston and Cambridge.

Between the boats, bridges, crowds and usually very cooperative fall foliage, this is Greater Boston showing off a little.

Boston Book Festival

For a decidedly less athletic October outing, the Boston Book Festival returns to Copley Square on Saturday, October 17 from 10 a.m. to 6 p.m.

The festival brings authors and readers together for a full day of free programming in the heart of Boston.

October 17 is actually a slightly ridiculous choose-your-own-adventure day this year. You can catch Head of the Charles, wander the Boston Book Festival or head to Medford for Harvest Your Energy.

Where I'd Go for Fall Foliage

You do not need to drive to Vermont to see fall colors.

This is reassuring news for anyone who has ever spent a beautiful October afternoon staring at brake lights on I-93 because all of New England decided to look at leaves simultaneously.

My JP Pick: Arnold Arboretum

The Arnold Arboretum is a personal favorite for me because I used to live in Jamaica Plain.

One of my favorite simple fall outings was walking through the Arboretum with a hot coffee and a pastry. There is something about JP in October that makes wandering around looking at trees feel like a perfectly legitimate weekend plan.

These days, I'd grab something from Viza Cafe or Fiore's Bakery before heading over. Viza is a newer South Street coffee shop serving Colombian coffee and pastries, while Fiore's is a longtime JP bakery nearby.

The Arboretum itself is free to explore, and because its collections include such a wide variety of trees, there is plenty to see as the season changes. You can keep it to an easy walk or head toward Peters Hill for a longer wander and views across the landscape.

For me, though, you don't really need an event. Coffee, pastry, trees. Done.

Mount Auburn Cemetery: Foliage With a Little Spooky-Season Energy

If you grew up outside New England, the idea of going to a cemetery specifically to take a walk and enjoy the scenery might sound a little strange.

Around here, it is surprisingly normal.

Historic cemeteries are woven into the landscape of New England communities, and Mount Auburn Cemetery in Cambridge is particularly special. It is both an active cemetery and an accredited arboretum, with winding paths, historic monuments, wildlife and an incredible collection of trees.

So newcomers and visitors are absolutely welcome to join us in the very New England pastime of recreational cemetery walking. Just remember that it is still an active cemetery, so give services and grieving visitors plenty of space and treat the grounds respectfully.

And if strolling through a beautiful historic cemetery surrounded by orange leaves feels just a tiny bit spooky in October, well, that isn't exactly a downside during spooky season.

To me, this is the kind of fall outing that feels very Greater Boston: history, nature, architecture and foliage all in one place.

Make the Most of Fall in Greater Boston

One of the things I love about Greater Boston is how different fall can look within a relatively small area.

You can spend one Saturday apple picking in Stow, the next watching marching bands take over Somerville and Cambridge, another walking along the Charles during the Head of the Charles, and finish the season cheering on runners at the Turkey Trot in Arlington.

And if you're considering a move, these kinds of days can tell you quite a bit about a community.

At the Santana Team, we've helped more than 1,600 clients across Greater Boston since 2014, and one thing we often encourage buyers to do is spend time in a town or neighborhood when they're not rushing between showings.

Walk down Main Street. Try the parks. Attend a community event. Take the train. Grab coffee. See what the place actually feels like on an ordinary Saturday.

Somerville, Cambridge, Arlington, Medford and Boston each offer their own mix of parks, transit, local businesses, arts, green spaces and community resources that all kinds of households can enjoy.

If your fall exploring has you thinking about a move, you can browse:

Somerville homes for sale | Cambridge homes for sale | Arlington homes for sale | Medford homes for sale

Or connect with our full team to talk about buying, selling or investing in Greater Boston.

Connect with the Santana Team

Event schedules, admission, crop availability and other seasonal information can change. This guide was updated with 2026 information available at the time of publication. Check individual event and farm websites before heading out.

FAQ: Fall Things to Do in Greater Boston

What are some of the best fall activities near Boston?

Apple picking, pumpkin patches, fall foliage walks and neighborhood festivals are some of the classic fall things to do around Greater Boston. Major annual events include the Head of the Charles, HONK!, Harvard Square Oktoberfest and the Boston Book Festival.

Where can you go apple picking near Boston?

Shelburne Farm in Stow, Russell Orchards in Ipswich, Smolak Farms in North Andover, Connors Farm in Danvers and Lookout Farm in Natick are among our team's picks for apple picking near Boston.

Where can you find pumpkin patches near Boston?

Shelburne Farm and Connors Farm both offer pumpkin picking along with other fall activities. Smolak Farms also includes pumpkin picking during its fall festival season.

What fall events are happening in Somerville in 2026?

Highlights include the Gilman Square Arts & Music Festival on September 12, What the Fluff? on September 19, HONK! from October 9–11 and SomerStreets: Monster Mash on October 18.

What fall events are happening in Boston in 2026?

The Boston Arts Festival is September 12–13, the Boston Local Food Festival is September 20, Head of the Charles runs October 16–18 and the Boston Book Festival is October 17.

What fall events are happening in Arlington in 2026?

Arlington Town Day is September 19, and the Arlington EATS Turkey Trot takes place November 8. The Santana Team is sponsoring the Turkey Trot and will be handing out coffee and donuts on race morning.

What fall events are happening in Cambridge in 2026?

Cambridge Arts Open Studios runs September 19–20, the Harvard Square Oktoberfest and HONK! Parade is October 11, and the Head of the Charles Regatta runs along the Cambridge and Boston sides of the river October 16–18.

What fall events are happening in Medford in 2026?

Medford's fall calendar includes Oktoberfest on October 3, Harvest Your Energy on October 17 and the Pumpkin Float and Lantern Parade at Wright's Pond on October 24.

When is the 2026 Head of the Charles Regatta?

The 2026 Head of the Charles Regatta takes place October 16–18 along the Charles River in Boston and Cambridge.