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 September of 2022]
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….”
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. 😉
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)
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!
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
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”.
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.
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
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.
One of my favorite restaurants in South End on the famous Tremont St. They serve delicious French cuisine in a nice, polished atmosphere.
The British refer to this time of year as “Autumn” while Americans typically refer to it as “Fall”.
3. Back Bay
Favorite Boston Fall Activities in Back Bay
Also known as “The Pru” by locals, Prudential Center is the 2nd tallest building in Boston. It’s very distinguishable in the rest of the city. You can see the building from far away.
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.
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.
If you’d rather dine somewhere else, you can view all the dining options at the Prudential Center here.
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. 😊
In 1765, the US opened its very first chocolate factory in Boston’s Dorchester neighborhood.
In October, you can decorate and carve out a jack o’ lantern to float at Frog Pond. What’s more Fall than that?!
I know what you’re thinking… What does Fall have to do with ice skating?! Well, my friends.. since Fall is technically November, if you really wanted (as I so often have), you can go ice skating!
Toward the end of Fall, it’s typically cold enough to go ice skating at Frog Pond, typically late Nov.
Check-in advance here before you go.
Located adjacent to Boston Common, the garden is a lovely treasure in Boston. So gorgeous during the Fall season and one of the best places to view the foliage. Walk across the little bridge and take it all in.
I love walking around the pond. It’s interesting to see the way the landscape changes from season to season. The scenery in Fall is just beautiful! You have to see it for yourself. Words will not do it justice.
Where are my Goodwill Hunting Fans at? They filmed one of Robin William’s most memorable monologues from the film at Boston Public Garden. Matt Damon and Robin Williams’ characters sat on one of the benches.
Shopping heaven! Newbury St. is like the Park Avenue of Boston. All the different stores you could ever want, a bit more high-end.
It’s a well-maintained street, clean and walkable. Definitely recommend shopping. A lot of luxury, high-end stores, and boutiques. Also spas, beautiful places, and restaurants. Be prepared to spend!
It’s right next to Boston Common, the whole area is very walking friendly. You’ll enjoy the foliage while shopping for your next cozy sweater. Me personally… I like going to Cartier and Tiffany’s. 😉
My friend and I went in September. I packed my picnic backpack with some homemade (gourmet, if I may) sandwiches and a bottle of prosecco. Shhh… don’t tell anyone. 😉
It was a chilly, windy day… perfect for the sailboats we were watching, probably not perfect to have a picnic. I sucked it up though and really enjoyed the lovely beginning to Fall.
On the other side of the Charles River in Cambridge. Home to MIT, Harvard, awesome shows, popup bars, nightlife, and restaurants. I’ll get into that another time. 😉
They have a lot of locations in Boston. Haven’t found a bad one yet. Their brunch and lunch items are yummy.
But, when I’m here, I usually go straight for the desserts.
One day, I just had a crazy sweet tooth.. and I was PMSing so I got literally one of everything… My excuse is that I’m trying to fatten up for the winter, lol. After having my sweets, my friend and I traveled up Newbury St. to look at pumpkins in Beacon Hill.
It’s a remarkable library and so gorgeous on the inside! Definitely worth a stop if you’re in Boston. You wouldn’t know it.. but there are some great food options on the inside that would appeal to any foodie regardless of whether you like to read or enjoy history.
For a quick, casual bite, they have a café toward the entrance of the library. Here, you can grab a coffee, tea, and pastries to go. You can even bring it outside to the libraries’ adorable courtyard hidden within the library.
It’s a lovely place to sit and take in the fresh air. It’s one of my favorite places to go in the city! I’ve been here at all different times of the year. Fall is one of my favorites. The vibe is much calmer and it’s relaxing.
- The Courtyard Tea Room
Within the courtyard is The Courtyard Tea Room, an elegant high tea establishment of the same name. They have books as menus which is just so cute and right up my alley!
- The Map Room Tea Lounge
If you want something a bit more adventurous and more laid back, there’s another place you can have drinks and lunch adjacent to the tea room called The Map Room Tea Lounge.
They serve tea, craft cocktails, lunch in a cool, historic setting with many objects to check out, and not surprisingly, maps. For you navigators and history lovers out there!
I’ve been to both and they’re some of my favorite hidden gems in the city! A Bostonian treasure.
If you don’t know me by now, I’m addicted to spas and love trying new experiences internationally.
When looking for a new place in Boston, I had read great reviews from a magazine for Viyada Thai Spa and wanted to check it out. If you haven’t experienced a Thai massage before, it’s more like a Chiropractic Pilates treatment than a typical massage.
You start off with some nice tea and hot towels after you sign in. Then, they provide you a cloth outfit to change into (shirt & pants). Clothes are kept on during the entire treatment while they work away your kinks one at a time. Softly squeezing and pulling on your ligaments to release built-up tension.
It sounds like a spa experience from hell but I promise, it’s actually really soothing. 😉 Afterward, I felt so loose and flexible, without the aches and pains I came in with.
I have Lupus so I always crave the sensation of someone squeezing and pulling my arms and legs so the Thai massage happened to be just what I was looking for.. and I didn’t even know it before I walked into this place.
I’ve received many Thai massages since and Viyada gave me one of the best ones I’ve had to date. This is interesting because this is a no-frills day spa. There aren’t any amenities.. just treatment rooms and a restroom. Sometimes simple just works. They focus on what they’re good at and they do it well! Will definitely return here.
Very relaxing experience! Would recommend for a simple, no-frills day spa.
More info for treatments here.
4. Long Wharf
Boston has many personalities. Long Wharf is the city’s seaport personality. When you’re ready to take a break, there is a lot of restaurant and bar options around.
I always enjoy taking a walk and having lunch while watching the boats come in and out of the harbor.
This is also where I took my day cruise from (below).
Fall in Long Wharf, Boston
One day in September, my friend and I decided to take a fun day cruise in Boston! We both lived in the city but wanted to experience the water.
After checking in at the designated spot, we hopped aboard. But, not before having our pictures taken. There was a photographer snapping souvenir photos to be purchased later, which of course, we did. 😉
We upgraded to a window table for water views.. kinda the whole point of taking a cruise. They also offer other upgrades for special celebrations.
The 3rd week of September was a lovely time to go, still sunny out, warm temperatures. I didn’t see any foliage as it was on the water, but it was nice to welcome the new season! You can go on the deck and take in the breeze, it was very refreshing.
The cruise I went on had a full buffet, champagne, a DJ, and a dance floor! We were dancing and drinking bubbly the whole time. It was so fun! We were the most fearless dancers there though no doubt.😉
In the end, you can order photos, which I ended up doing.
I really enjoyed the experience. If you like music, drinks, food, dancing, and great views, this is a great time!
It’s a beautiful 5-star waterfront hotel and one of my favorites in Boston. When I stayed here, I just wanted to get away/ Even though I lived in Boston at the time, lol.
I spent the stay just relaxing, ordered chocolate-covered strawberries and champagne. It was a little “me” date.
At night, the hotel has live music downstairs in the lounge. When I was there, they had a jazz band playing which I loved dancing to!
The next morning, I decided to be lazy. When I woke up, I ordered room service and lounged feeling like a tourist in a new city. It was a nice stay.
This 5-star hotel is lassy, clean, upscale. You can’t beat the location, which is beautiful. Get a room on the water if you can.
The hotel has a nice seafood restaurant downstairs where I enjoyed a delicious lunch before checking out. It has a nice atmosphere.
Downtown Boston has a lot going on. It’s home to a lot of the historical landmarks you’ll find on the Freedom Trail.
Fall Favorites in Downtown Boston
Open for the last 65 years Kane’s Donuts is the “Donut OG of Boston”. I always seem to order the whole damn dozen. There was a period where I wouldn’t leave my apartment for days and I’d just shamelessly have these delivered.
I originally found them because they were the only donut shop that offered Gluten Free donuts that didn’t taste awful. They also delivered.
Love this donut place! They’re tasty, they deliver, and have a great selection of Gluten-free options too.
6. North End
You can’t go to the North End without eating. The North End neighborhood is basically the Little Italy of Boston. Nothing says warm, cozy, and Fall to me more than hardy comfort food… Find a place and Mangia!
Fall Favorites in the North End
Although this Italian place was super tiny. Like “rubbing elbows with your neighbor at the next table” tiny, it had yummy food. My friend and I had a lovely dinner here.
Tasty Italian food but in a very cramped setting. Made the overall experience uncomfortable.
The staff wasn’t very friendly.
Stay tuned for my next blog about Boston and more North End foodie finds.
This market is open year-round and has a great selection of fresh, local food like bread, cheese, honey, and produce, as well as seasonal treats and specialty items for home and beauty care.
- Red Apple Farm
It was nice to walk around and check out the different vendors. I decided that since it was Fall, I would get into the spirit with some yummy fresh apple cider donuts and hot cider from Red Apple Farm which were great.
- Jennifer Lee’s Bakery
Not so great, my worst vegan, Gluten-free, dairy-free experience at Jennifer Lee’s Bakery. Ucckkk. Vowed to never do that again, or Vegan in general… lol. I don’t know how they do it… I found out later that my friend was going to get my birthday cake made here. I was like thank goodness you didn’t. 😊
PLAN YOUR TRIP
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Have you experienced Boston in the fall? Which one of the Boston Fall Activities are you looking forward to?
What is a favorite Fall memory of yours?
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