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For me, experiencing Fall foliage in Boston 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, NYC, 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 Fall adventures in Boston! Wait… I get to share my love for Fall and Boston with you?! Heck yes! Double whammy! 😊

Just a warning, a lot of my favorite ways to celebrate Fall and a lot of the Boston adventures I talk about happen to involve 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. 😉

FACT: Real Girls Love Fall Themed Activities & Foodie Finds

“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

When Should I Visit Boston in the Fall?

The best time to go to Boston to experience Fall is when the Fall foliage peeks from the end of September to mid October. 

Personally, early October just so happens to be my favorite time to enjoy the season. And not because it’s my birthday… well.. okay, yeah, maybe because of that too. 😉 Foliage is the gift I wait to receive all year long. 

How to Spend Fall in Boston

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 Fall activities, and transforming my wardrobe with enough themed outfits to wear for those 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.

Boston Public Market

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 more hot! Plus.. green trees… ugghh.. boring! Lol

Why have Summer when you can walk past a brownstone that looks like this?!

So, I really appreciate 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.

Best Neighborhoods to Experience Fall in Boston

One of the biggest draws for me when it came to this city.. and especially during the Fall season, is it’s 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 it’s glory! 😊

I love when Bostonians get into the Fall spirit!

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.

My Favorites: 

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.

South End

I lived in this neighborhood for a few years and really liked it. It’s 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 non fat 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”.

My Fall Favorites:

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 childrens 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 fresh 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.

It’s broken up into 3 sections separated by 2 long buildings that house studios and art galleries that are open to the public.

  • Section 1: Traditional Farmer’s Market

  • Section 2: Food Trucks & seating area, separated by 2 long buildings.
  • Section 3: More of a craft fair

Check out SOWA market 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..

I’m obsessed with street style corn!!!

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 here more than any other restaurant in the city since it was so close to my apartment, lol.

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.



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

Back Bay

My Fall Favorites: 

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.

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. 😉


Saks, Papyrus, MAC, Sephora, Kate Spade, Sugarfina, & Canada Goose.. all at the Pru.

Oh snap! I found my pair..
Got this genius emergency drink kit so I could make myself a quickie Fall cocktail when I got home!

All stores here.

Time to Eat! 

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 dining options here

One of my favorite Boston restaurants with a view, Top of the Hub, is sadly no longer in business.

Who knows, maybe at the time that you’re reading this there’s a new restaurant! 



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

You learn a lot of 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 this place. 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.

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 just people.. not quite as exciting.. lol.

 Fall at Boston Common

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.

It’s not unusual to run into a person feeding a squirrel.. sometimes, from their arm… lol

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 Ave. of Boston. All the different stores you could ever want, a bit more high end.

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. 😉

Okay, admittedly I have a thing for picnics. Finding a shady, tree to sit under while admiring the Charles River makes The Esplanade a lovely spot for a Fall picnic!

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.. lol. 😉

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 is Cambridge, home to MIT and 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 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 year. Fall is one of my favorites. The vibe is much calmer and it’s relaxing.

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!

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 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 the best one I’ve had to date. Which 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.

Treatments here.

 Long Wharf

Boston has many personalities. Long Wharf is the city’s seaport personality. When you’re ready to take a break, there are 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).

My Fall Favorites:

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.

We got to see more of Boston’s gorgeous seaport from the upper deck.

The cruise I went on had a full buffet, champagne, a DJ & 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.😉

At the end, you can order photos, which I ended up doing.

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..

Was able to enjoy nice views of the water from the comfort of my cozy room which I really liked.

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.

The hotel has a nice seafood restaurant downstairs where I enjoyed a delicious lunch before checking out. It has a nice atmosphere.

The scallops were tasty

Downtown Boston has a lot going on. It’s home to a lot of the historical landmarks you’ll find on the Freedom Trail.

A Fall Favorite:

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.

No I wasn’t PMSing… lol

I originally found them because they were the only donut shop that offered Gluten Free donuts that didn’t taste awful.. that also delivered.

My favorite donuts to get in the Fall are their apple cider (made w/ apple cider) and pumpkin spice donuts. They even have non GF options like maple bacon and crème brulee. Screw GF! OMG! 😊

North End 

You can’t go to the North End without eating. This 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!

My Fall Favorites:

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..

I started off with the mussels which were delizioso!

It was very Fall themed in there! They even had 2 giant pumpkins weighing 1,000 lbs. total. The market was taking suggestions for pumpkin names. How cute!

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 the home and beauty care.

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.

Not so great was my worst vegan, gf, 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. 😊

And now, for my favorite part…

Real Girl Reviews

The Good, the Bad, & the Ugly

Blackstones Gift Boutique 

Great for souvenirs and gifts. Over the holidays, they accept returns even if you didn't purchase the gift at their store which I thought was interesting.

Beacon Hill Bistro 

I've definitely had better food and better service elsewhere but they're conveniently located.


They're definitely not cheap. But, for a gift shop, they have a diverse selection of items from artists internationally and have unique items you don't typically find everywhere (i.e. pro gay parents childrens books). If you're not progressive, it's probably not the shop for you.

SOWA Market

Great seasonal market in South End for fresh food and shopping. Dogs are welcome.

The Buttery

Cozy place for brunch.


Portions are small for the price and the place can get quite cramped & loud as it gets busy, but the food is delicious. Perfect place for a snack and some drinks before hitting another dinner spot.


I love the different French food options here. I've not had a disappointing meal yet. You can order casual bar food or full on dinner.


One of my favorite French restaurants in the city. Love their menu and restaurant set up. It has a very cozy feel to it and lots of ambiance.

The Prudential Center

Great selection of shops, restaurants, and activities located under one building.

L.A. Burdick Chocolate

Great holiday offerings! I like giving them as gifts only I somehow end up snuggling up next to the person and eating most of them.. so I guess they’re not so great as gifts afterall.. unless it’s to yourself, lol. 

Boston Common

Great park for walking and ice skating!

Boston Public Garden

Beautiful park and walking area! Especially gorgeous in the Fall. A Boston must see!

Newbury St.

Very well maintained street, clean and walkable. Definitely recommend for shopping. A lot of luxury, high end stores and boutiques. Also spas, beauty places, and restaurants. Be prepared to spend! 


Very clean, walkable waterfront park. Very nice for picnics, jogging, riding bikes, etc.

Tatte's Bakery & Cafe

One of my favorite bakeries. They always have something seasonal and tasty. It can be a bit of a cluster F trying to get a table but if you can find one, it's a nice morning or afternoon.

Boston Public Library

The Courtyard Tea Room is absolutely lovely and perfect for afternoon delights. 

The Map Room Tea Lounge is definitely worth checking out.

Viyada Thai Spa

Very relaxing experience! Would recommend for a simple, no frills day spa.

Boston Harbor Day Cruises

I really enjoyed the experience. If you like music, drinks, food, dancing, and great views, this is a great time!

Boston Harbor Hotel

5 star hotel. Classy, clean, upscale. You can't beat the location, which is beautiful. Get a room on the water if you can.

Rowes Wharf Sea Grill

Tasty seafood restaurant on the water within the hotel. 

Kane's Donuts

Love this donut place! They're tasty, they deliver, and have a great selection of GF options too.

Boston Public Market

Great market for seasonal, local products from farmers and artists.


Tasty Italian food but in a very cramped setting. Made the overall experience uncomfortable.

The staff wasn't very friendly.

Plan Your Trip

Get My Fall Boston Google Maps Itinerary Here!

You can also copy, print, share, or download it!

What is a favorite Fall memory of yours?

I love hearing from my readers! Feel free to comment below and let me know if you enjoyed my post. 

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geeves fall illustration



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