How to spend a perfect fall day in Boston

Fall in New England is my absolute favorite time of year. The weather is amazing, not too hot but not too cold, and almost always sunny or partly cloudy. Boston is especially beautiful when the crisp air rolls in and leaves begin to fall.

If you’re new to the city, or just looking for some new suggestions on how to spend a fall day in Boston, look no further! I’ll be breaking down the best activities and things to see based on the time of day- that way you avoid all of the tourists (as much as possible) and the commuters too!

Early Morning Suggestions: 7 a.m.- 12 p.m

Get away from the main commuting streets in Boston (near North and South station) and you’ll find that Boston is quite peaceful and rather quiet in the mornings. When I used to work on State St. I loved to take the “long way” some mornings to see historical streets like the one below uninterrupted.

Get up a little bit earlier than normal, grab a coffee at one of Boston’s many cafes, and pick your spot in the city to enjoy a nice morning stroll or simply sit at a bench and enjoy your surroundings.

My top 2 areas I suggest are:

  • Newbury Street- SO many little cafes. Take your pick and then stroll down to the Boston Public Gardens to enjoy your morning coffee with an excellent view.
  • Haymarket/Faneuil Hall Area- Get off the Orange Line at Haymarket and stop into Boston Public Market. There, you’ll find stands filled with donuts, bagels and breakfast sandwiches, and a couple of coffee spots. Then, stroll down Marshall Street (pictured below) for an uninterrupted photography session or just a great view.

After you’ve grabbed some breakfast, the morning (pre-lunch) is generally the best time to see sights you’d like to photograph, as many tours don’t begin before 12 pm and most commuters do not typically pass through areas I’ll mention below

Some of my top spots to go for photography fun are:

  • Acorn Street and Beacon Hill in general
  • Boston Public Gardens
  • Long Wharf
  • North End- specifically Paul Revere Mall + Old North Church and North Square
Acorn Street- taken in the afternoon with all of the tourists! Go early 🙂

Lunch + Mid-Afternoon:

Now, after you’ve spent the morning walking around and burning some serious calories stop at these spots to refresh and refuel!

  • North End: Lucia or Trattoria il Panino
  • Haymarket/Faneuil Hall area: Zo’s, Pita Thyme, Bostonia Public House
  • Copley/Prudential: Earls, Anna’s Taqueria, Citrus & Salt
  • Newbury Street: Buttermilk and Burbon, Stephanie’s on Newbury

After you’ve fueled up, these are my top mid-afternoon spots and activities:

  • Take some type of walking tour: a photography tour, a tour of the freedom trail, Duck Boats
  • Visit one of Boston’s many museums: ICA, MFA, Isabella Stewart Gardner, Boston Public Library
  • Go Shopping: Check out all of the shops in Downtown Crossing, Newbury Street, and the Prudential Center
  • Pack a picnic or stop into Kured on Beacon Hill to enjoy a charcuterie board at the Public Gardens

All of the activities I’ve mentioned are sure to take you a couple of hours, so now let’s talk about when then sun goes down!

Sunset + Night Time:

Now that the sun goes down, your touristy part of the day is mostly over, but the fun isn’t! There are SO many fun places to eat, drink, and enjoy some entertainment.

Now, lets talk about some of the top spots for a pre or post dinner cocktail:

  • Lookout Rooftop Bar in Seaport– Unreal spot to enjoy the skyline as the sun sets
  • The Landing @ Rowe’s Wharf- Also fantastic drinks and right on the water
  • Sam Adam’s Tap Room– Faneuil Hall
  • City Winery– North Station Area
  • Earl’s– Prudential
  • Cisco, Harpoon, Nightshift– all have outdoor beer gardens in the city (mostly Seaport area)

Some of my favorite dinner spots include:

  • South End: Barcelona Wine Bar- Tapas style, authentic spanish
  • North End: Lucia, Giacomo’s, Fiore, Bricco, and Trattoria il Panino. Stop by Mike’s Pastry or Bova’s for dessert afterwards!
  • Seaport: Gather, Legal Sea Food, The Smoke Shop BBQ, Tuscan Kitchen
  • Newbury/Copley/Boylston: Earl’s, Eataly, Del Frisco, Abe & Louie’s, Citrus + Salt, Lolita’s
  • South Boston: Capo, Lincoln Tavern, The Broadway, Publico, Loco
Tortellini Pesto from Lucia’s

Now after dinner, I’m sure y’all aren’t ready to leave the city quite yet- so here are some of my favorite evening activities:

  • Check what’s going on at the TD garden. Especially during weekends, there’s bound to either be a sports game or a performance
  • Improv Asylum- North End. Super cheap improv comedy show that is absolutely hilarious
  • See a play
  • See a Sox Game: October is playoffs season for the Red Sox!
  • Check out the bar scene: Boston has some of the best pubs and clubs, definitely check them out! Some of my favorites include:
    • Bell in Hand- Haymarket
    • The Greatest Bar- North Station Area
    • Howl at the Moon- Financial District
    • Cask ‘n Flagon- Fenway
    • Coogan’s- Faneuil Hall area
    • Lookout rooftop bar- Seaport
    • Lincoln Tavern & Capo- Southie

Now, I made this super open ended to ensure y’all could mix and match activities, places to see, and places to eat based on your interests, budgets, and food preferences. If you’re new here, I’m confident this will give you not just one day’s worth of things to do! And if you’re a local like me, hoping that you found at least one new activity or restaurant that you didn’t know beforehand!

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