Boston in the fall is pure magic — the kind of trip you’ll still be daydreaming about years later. Between the history, the food, the fiery foliage, and the cozy neighbourhoods, it’s hands-down one of the best US cities to visit in autumn. I left Boston with about 500 photos of pumpkins, a serious clam chowder addiction, and a promise to myself to come back next fall. If you’re on the fence about visiting — go. Trust me, you won’t regret it.

Ready to book your fall trip? Check out flights with United Airlines, grab a Go City Boston pass, and treat yourself to a stay at the Boston Harbor Hotel for the ultimate autumn getaway.

Plan your fall trip to Boston:

  1. Why Visit Boston in the Fall?
  2. Getting to Boston from London
  3. Where to Stay in Boston in the Fall
  4. Handy Fall Travel Tips for Boston
  5. Best Things To Do in Boston in the Fall

best things to do in Boston, USA – boston in the fall

Why Visit Boston in the Fall?

Boston in the fall is like stepping straight into a movie set. Think crunchy leaves, golden sunlight, pumpkins on every stoop in Beacon Hill, and the smell of cinnamon and clam chowder drifting through Quincy Market.

I visited Boston in early November and honestly? It was one of the best city break trips I’ve ever taken. Not only was the weather dreamy (24ºC one afternoon — yes, in November!), but the city just feels alive this time of year. You get the fiery foliage, a few spooky Halloween leftovers, and way fewer crowds than in summer.

If you’re planning your first Boston fall trip, here’s my ultimate guide to the best things to do in Boston in autumn — with plenty of personal tips, foodie stops, and cozy recommendations. If you're travelling to Boston at any other time of year, I've also created this list of the best things to do in Boston (anytime) and 5 Day Boston Itinerary for First-Timers.

Getting to Boston from London

From London, it’s super easy — direct flights from Heathrow to Boston Logan International Airport take just 6–7 hours. United Airlines even has a daily service, and their Polaris Business Class is worth the splurge if you want to land well-rested.

Logan is just 15 minutes from downtown, so you can be wandering Beacon Hill pumpkins the same day you land.

👉 Book your flight from London to Boston

 

Where to Stay in Boston in the Fall

Fall is a popular (and pricey) time in Boston, so book early.

If you're planning a solo trip to Boston – read my guide for tips on how to save money.

22 best things to do in Boston, USA

Handy Fall Travel Tips for Boston

  • Pack layers. Boston fall weather can swing from warm sunshine to chilly evenings. (it was 24ºC when I was there – so be prepared for all weathers!)

  • Book early. Hotels and tours fill up quickly around Halloween and foliage season.

  • Get a Go City Boston Pass. It’ll save you money (up to 50% discounts) on museums, stadium tours, and more.

  • Wear comfy shoes. Boston is super walkable — you’ll easily rack up 20k steps a day.

  • Don’t skip the food. From lobster rolls to pumpkin spice everything, Boston’s fall foodie scene is unreal. Check out my food guide to Boston for tips on budget-friendly eats and food tours.

22 best things to do in Boston, USA. Acorn street and beacon hill in the fall – first time in Boston

Best Things To Do in Boston in the Fall

1. Wander Through Beacon Hill

If I could bottle up the essence of Boston in the fall, it would be Beacon Hill.

Acorn Street is one of the prettiest (and most photographed) streets in the US — cobblestones, gas lamps, and historic brownstones dressed up with pumpkins, wreaths, and golden leaves.

👉 Personal tip: I visited the day after Halloween and the stoops were still decorated with jack-o’-lanterns, which gave the whole neighbourhood a storybook vibe. Come October for peak pumpkin spotting.

2. Explore Boston Common & Public Garden

Boston Common is the oldest city park in the US, and in autumn it’s a sea of reds, oranges, and yellows. Take a stroll, grab a coffee, and people-watch under the trees.

Right next door, the Public Garden is equally beautiful. The swan boats stop running in September, but the crisp air and crunchy leaves more than make up for it.

💡 Travel tip: Pack a picnic blanket and book — spend an hour relaxing and soaking up the sunshine (It's giving Gilmore Girls vibes!)

3. Walk the Freedom Trail

Yes, it’s touristy. But it’s also one of the best things to do in Boston in the fall because you get 2.5 miles of history and foliage all rolled into one.

Starting at Boston Common, the Freedom Trail connects 16 historic sites — including Granary Burying Ground, Faneuil Hall, and Paul Revere’s House.

I took a guided tour and loved hearing quirky stories from Boston’s past while wandering through leafy, colourful streets.

4. Visit Granary Burying Ground

Okay, I know a cemetery might not scream “fall fun,” but trust me: Granary Burying Ground is one of the most atmospheric places in Boston in autumn.

Founded in 1660, it’s the resting place of big names like Samuel Adams, Paul Revere, and John Hancock. With the fall leaves scattered across centuries-old gravestones, it’s hauntingly beautiful.

And fun fact: it’s the only place in the world where you can drink a cold Sam Adams while looking at a cold Sam Adams (thanks to the pub across the street).

5. Catch a Game at Fenway Park

Sports fans (and even non-sports fans), listen up: catching a Red Sox game at Fenway Park is unforgettable. The regular season runs through September/early October, so if your trip lines up, grab tickets.

I did a stadium tour, and while it was great, I have to admit — nothing beats seeing a game live with the whole crowd buzzing.

6. Warm Up with Clam Chowder & Lobster Rolls

Boston in the fall = comfort food heaven.

You have to try a classic New England clam chowder (creamy, cozy, and best eaten on a chilly day) and a lobster roll (buttery perfection).

👉 My top picks:

  • Union Oyster House (the oldest restaurant in America, and their lobster roll is chef’s kiss)

  • Time Out Market Boston for casual bites — I devoured the truffle pasta, but there’s also sushi, Philly cheesesteaks, and lobster mac & cheese.

7. Take a Food Tour of Chinatown

One of my favourite experiences was joining a Chinatown food tour. I tried dim sum, moon cakes, boba tea, and even learned about herbal teas and traditional medicine.

The best part? Wandering through this neighbourhood in fall, with colourful street art and lanterns popping against the crisp autumn skies.

8. Step Inside Boston Public Library

If you’re a bookworm like me, this is non-negotiable. The Boston Public Library is basically Beauty and the Beast vibes IRL. Think grand marble staircases, tall arched windows, and rows of cozy reading nooks.

I recommend visiting in the morning when the light pours in through the windows — perfect for photos.

 

9. Day Trip to Salem

Fall and Salem? Name a better combo.

Just 30 minutes from Boston by train, Salem is famous for the 1692 witch trials, but in autumn it turns into full-on Halloween central. Think haunted houses, witch museums, quirky shops, and pumpkins on every doorstep. You can also book a day trip and Witch Trials tour to Salem which sounds incredible!

I wish I'd had time to visit during my trip and I would go back specifically to experience the magical (and spooky) feel. 

 

10. Whale Watching from Boston Harbor

Yes, you can still go whale watching in the fall (season usually runs through October) and spot humpbacks and dolphins from a catamaran, what an incredible thing to experience!

Even if the whales don’t show, the skyline views from the water at this time of year are stunning.