Planning your Boston Fall activities? See how to enjoy Boston in the Fall in these 6 neighborhoods.

For me, experiencing Boston in the Fall and its fall foliage is like viewing your favorite photos in a scrapbook. That’s where it should be… it’s just so pretty!

I wasn’t always so starry-eyed though! My first impression of the city was that the colder months are far longer than the warmer ones. So, I was surprised how much the city grew on me after living there for a few years.

Boston spoke to the young person in me who sought adventure and excitement but who also craved history and a charming landscape… It was a very different feel from the city I spent a lot of time in, New York City, which was very shiny, modern, new, and constantly updating itself to meet the latest trend.

What I didn’t realize was how beautiful and fun Boston could also be in the Fall, my favorite season! And now I share with you, my favorite Boston Fall activities!

Wait… I get to share my love for Fall and Boston with you?! Heck yes! Double whammy!

[This post was originally posted September of 2020. Updated August of 2022]

Just a warning, a lot of my favorite ways to celebrate Fall in Boston involves food. 

What can I say… I go where the belly goes, lol. Maybe you can relate, but my belly feels so cozy in the Fall so it wants to eat and eat!!  

A lot of the restaurants I’ve listed below offer seasonal menus. You’re sure to find some good grub that matches your appetite for Fall foliage!

Are you that one weird person who doesn’t enjoy eating? No worries. I have plenty of non-food things, too. 

“For no matter how they might want to ignore it, there was an excellence about Boston, an air of reason, a feeling for beauty, a memory of something very good, and perhaps a reminiscence of the vast aspiration of man which could never entirely vanish….”

Arona McHugh

Boston in the Fall

When Should You Visit Boston in the Fall?

The best time to experience Boston in the Fall is when the Fall foliage peaks from the end of September to mid-October. 

Personally, early October just so happens to be my favorite time to enjoy the autumn season. And not because it’s my birthday… well.. okay, yeah, maybe because of that, too.

Fall foliage is the gift I wait to receive all year long. 

How to Spend Boston in the Fall

Okay, now I don’t know about you… but, I have a little integrity when it comes to my Fall game. Before the first colored leaf even drops, I’m pulling out all the stops. (I did not mean for that to rhyme, just cool like that.. lol)

Indoors, I’m putting together Fall charcuterie boards, baking apple pie, and sipping hot cider while decorating my whole apartment.

Outside, I’m hitting up every joint in town that gives me the warm and cozies… hunting for new Boston Fall activities, and transforming my wardrobe with enough themed outfits to wear for those fall activities. It’s as if the chill in the air rewires my brain, sending messages to my subconscious to switch me from one season to the other.

Let me be real with you… I start planning Fall during the Summer… I can’t wait for it to be over most of the time, lol… You probably can’t relate. I prefer warm and comfy to just hot.. and then hotter! Plus.. green trees… ugghh.. boring! Lol

So, I really appreciate it when fellow Fall lovers honor the season and go out of their way to bring that cozy vibe to the city so we can all enjoy it!

FUN FACT

Boston is named after a town in England. The settlers decided to stick to what they knew and kept the name. How very original.. lol.

6 of the Best Neighborhoods to Experience Boston in the Fall

One of the biggest draws for me when it came to Boston, and especially during the Fall season, is its walkability quality. Pick a neighborhood, bundle up and stroll along the quaint cobblestone sidewalks. Savor the crisp chill in the air as the leaves crunch under your feet.

You’ll quickly realize that Boston is full of cute boutique shops, never-ending restaurant options, historic monuments, and gas lanterns lining the streets. That’s the charm of the city.

The beautiful brownstone walk-ups are usually seasonally decorated with gourds and harvest leaves which makes for the perfect backdrop to enjoy the foliage. It’s Autumn in all its glory!

1. Beacon Hill

Beacon Hill is one of my favorite neighborhoods in Boston. It’s the kinda charming place you sip a pumpkin spice latte while boutique shopping. To me, this neighborhood is quintessential Boston.

Favorite Boston Fall Activities in Beacon Hill

I love supporting small businesses. This is one of my favorite places to pop into when I’m in Beacon Hill. It’s a nice shop with a variety of treasures. Here, I’ve shopped for gifts as well as seasonal things for my home.

When you’ve shopped till you’ve dropped, snuggle up inside Beacon Hill Bistro located nearby. I stopped here for lunch after a day of shopping.

2. South End

I lived in this neighborhood for a few years and really liked it. South End is commonly known as the “hip”, gentrified part of Boston. There are lots of restored Victorian brownstone buildings and pretty walking areas with an English resemblance.. also moms with their $800 strollers and nonfat soy lattes. Lol… can’t relate. They have some great shops here too though.

As in any big city, avoid walking at night solo. South of Huntington can be a little “rougher”.

Check out my Amazon shop page to shop the things listed for each traveler in this blog!

Favorite Boston Fall Activities in South End

I like coming here for Fall! They have gifts crafted by more than 75 artists and creators from around the world. Also, cute “progressive” baby stuff… like children’s books with a baby’s 2 dads as the central theme. Was impressed with their “times are changing” selection. Got some stuff for my cousin’s baby girl here.

Every Sunday, May – October, SOWA (South of Washington) features local artists and craftsmen selling their wares.

It’s a cross between a farmer’s market and a craft fair. There are several food trucks offering everything from Vietnamese to craft sandwiches and crepes of the day.

You can get freshly baked food, seasonal produce & flowers, crafts, art, handmade gifts, etc. It’s a great place to wander around to have breakfast or an early lunch. I like to get donuts and coffee before making my way around to everything.

The SOW Market is broken up into 3 sections separated by 2 long buildings that house studios and art galleries that are open to the public.

• Section 1: You’ll find a traditional farmer’s market

• Section 2: Food trucks and seating area that are separated by 2 long buildings.
  
• Section 3: More of a craft fair

Definitely, check out the SOWA Market in Boston in the Fall!

This was only a few blocks from where I lived. I loved coming here for brunch on Sundays! What makes it even better is the fireplace downstairs. It’s a small cozy place with a relaxed vibe. Like the kinda place Harry would bump into Sally.

I used to come here all the time because it was literally right down the street from my place. They serve tapas here.. which are all for the most part really yummy.. also pretty small.

You could easily spend $200 to get your fill… I know I have. Lol.. But the ambiance is nice, sometimes it gets a bit crowded at night. If you wanna try it, the day is best when it’s less noisy. They also have a bar.

This is one of my favorite restaurants in Boston. I probably went there more than any other restaurant in the city since it was so close to my apartment, lol.

NOTE: Gaslight has since changed ownership and name. It is now called “Brasserie” and is just as delicious.

They serve French cuisine. The duck is my favorite.

One Fall, one of my closest friends, John, came into Boston for my birthday and we had a cozy dinner here.

One of my favorite restaurants in South End on the famous Tremont St. They serve delicious French cuisine in a nice, polished atmosphere.

FUN FACT

The British refer to this time of year as “Autumn” while Americans typically refer to it as “Fall”.

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3. Back Bay

Favorite Boston Fall Activities in Back Bay

Also known as “The Pru” by locals, Prudential Center is the 2^nd tallest building in Boston. It’s very distinguishable in the rest of the city. You can see the building from far away.

Here, you’ll find a lot of great stores and restaurants. I like spending my time here.

You can shop for your new Fall wardrobe and new makeup shades for the season! Or get a head start on your holiday shopping list, that’s what I always do.

Shop New England Fall Fashion

I’ve got the perfect looks for you! You can shop my favorite Fall looks directly here.

All at “the Pru”, you’ll find Saks, Papyrus, MAC, Sephora, Kate Spade, Sugarfina, and Canada Goose.

For more info on the stores, click here.

• Where to Eat at Prudential Center: Earl’s

They also have a great selection of restaurants at The Prudential Center. After an exhausting day shopping, my best friend and I stepped into Earl’s for some lunch.

They have a downstairs and upstairs option. I like dining upstairs for a view. I ordered sushi and an Old Fashioned, my signature drink.

When I was there, they had different takes on the Old Fashioned which was awesome!

If you’d rather dine somewhere else, you can view all the dining options at the Prudential Center here. 

• Skywalk Observatory

Speaking of views… The Skywalk Observatory is 360 degrees of sheer awesomeness. It’s on top of the Prudential Center. I would recommend doing this activity at the beginning of your Boston trip.

You learn a lot about the surroundings and see where things are located on the live map. There’s a lot of fun facts you can learn too. The foliage views are incredible.

Okay, first things first, time to pregame. You’re gonna need fuel to walk around the city. What’s cozier than chocolate?

I’m obsessed with L.A. Burdick. As soon as I walk in and get a whiff, it brings out the crazy in me. What I love about L.A. Burdick is that it has an old-fashioned feel to it… almost like a chocolatier shop from Paris.

They make some of my favorite chocolates. Many of which are European-inspired and handmade. I often buy several boxes just for myself. But, I can’t leave without sitting down for a cup of hot chocolate and a piece of cake first.

FUN FACT

In 1765, the US opened its very first chocolate factory in Boston’s Dorchester neighborhood.

Established in 1634, Boston Common is America’s Oldest Public Park! How cool is that? There used to be a lot of farm animals roaming the fields. Now it’s just people, so not quite as exciting. lol

• Pumpkin Float

In October, you can decorate and carve out a jack o’ lantern to float at Frog Pond. What’s more Fall than that?!

• Ice Skating