Ultimate Fall Weekend in Boston: Things to Do in Boston in the Fall
This trip marked the first time my sister and I traveled together, just the two of us. She was a college sophomore, and her fall break conveniently aligned with a holiday I had off from work in October. Now, it’s become our tradition to take a trip each fall until she graduates!
We spent an amazing long weekend exploring Boston and Salem. While we had visited Boston as kids, it had been ages, and neither of us had ever been to Salem—so it felt like the perfect blend of familiar and new. Salem, with its rich history and Halloween charm, was the ideal destination to kick off October and fully embrace the autumn spirit. If you’re planning a day trip to Salem, check out my dedicated Salem blog post for all the details and insider tips!
Welcome to Boston, baby!!!! We had a blast exploring this city—sightseeing, walking around, and exploring! There’s just something magical about Boston in autumn. From the pumpkins and mums decorating the charming brownstones to the crisp breeze coming off the harbor, it’s the perfect destination to kick off the season. In this post, I’ll be sharing all the highlights from our trip, plus the best things to do in Boston in the fall. Let’s start with where to stay!
Where to Stay in Boston
The Copley House
My sister and I stayed at The Copley House in the Back Bay, which is situated in a beautiful brownstone. It’s on the more affordable side for such a prime location, and I’d recommend it for a weekend stay. The rooms are small, but we spent most of our time out exploring the city anyway. A funny memory from our trip—we accidentally booked a room with a twin bed, but it only added to the adventure!
The Colonnade Hotel
The Colonnade Hotel is a sleek, modern hotel in the heart of Boston’s Back Bay neighborhood is a great option for those looking to stay centrally.You’ll be close to landmarks like the Boston Public Library and Prudential Center. We spotted this hotel while walking and I’d love to give this one a try.
Things to Do in Boston
Explore Boston Common
Boston Common is a must-see, especially in the fall when the leaves start to change. It’s the oldest public park in America, established in 1634, and covers 50 acres in the heart of the city. You can stroll through the scenic paths, relax by the Frog Pond (which becomes a skating rink in winter), or have a picnic on the lawn. The Common is perfect for soaking in some fresh air, enjoying the fall colors, and even taking a moment to learn a bit of history in this iconic Boston landmark. After you stroll this park – hit Beacon Hill! It’s not far!
Walk Around Beacon Hill
Beacon Hill is an iconic, historic neighborhood with cobblestone streets, charming old architecture, and quaint boutiques. Take your time strolling around, snapping photos, and popping into shops.
Look at how cute this little market was that popped into!!
For brunch, we dined at Bin 26 Enoteca, a cozy spot offering Italian-inspired dishes and an extensive wine list. Sitting outside, we enjoyed the beautiful fall weather and the charming atmosphere of Beacon Hill. It’s the perfect place to relax and people-watch after exploring the area.
After brunch, we popped into Beacon Hill Books & Café, a charming bookstore with a beautiful inside and so many books to explore.
Beacon Hill was such a charming, vintage, small heartbeat in the big city of Boston. It was like a breath of fresh air. If a quaint, small town feel is your vibe, you’ll definitely want to checkout Beacon Hill.
Boston Public Library
Boston’s Public Library, established in 1848, is a must-see. It’s one of the oldest and largest public libraries in the U.S., and its gorgeous architecture makes it a destination in itself. Take a moment to admire the grand marble staircase, stunning murals, and its peaceful courtyard, which feels like a hidden gem in the city. It’s the perfect place to sit with a book or just soak in the historic beauty.
Shopping on Newbury Street
If you’re into shopping, you can’t miss walking down Newbury Street in the Back Bay area. This mile-long stretch is filled with high-end shops, local boutiques, cafes, and art galleries. Whether you’re window shopping or picking up something special, it’s the perfect spot for a leisurely afternoon.
Explore the North End
The North End, Boston’s historic Italian district, is a must-visit. Before dinner, we stopped by the beautiful Old North Church, which played a key role during Paul Revere’s midnight ride. We then wandered the streets, soaking in the lively atmosphere, and found a charming restaurant with outdoor seating for some fresh pasta. The open-air dining experience was perfect, allowing us to enjoy the crisp fall breeze.
I remember walking by Euno Ristorante. We didn’t eat here but it looked so cute and cozy! It was kind of hidden away, if you are looking for a more cozy, romantic vibe. I don’t think you can go wrong with any Italian restaurant you stumble upon in the North End!
For dessert, you have to try a cannoli from the two most famous spots in town—Mike’s Pastry and Modern Pastry. Yes, the lines are long, but it’s all part of the experience! We met some fun people while waiting, and it was totally worth it. Both cannolis were delicious, but we leaned slightly toward Mike’s because they’re bigger (and who can say no to more cannoli?). But honestly, try both if you can!
Boston Tea Party Ships & Museum
Though we didn’t get a chance to do this, I wish we had! The Boston Tea Party Ships & Museum lets you experience one of the most famous events in American history—and yes, you can actually throw tea into the Boston Harbor (the tour takes place along the Fort Point Channel, which connects to the harbor). It’s a hands-on way to learn about history, and I’m definitely adding it to my list for next time.
Walk Through Quincy Market
Quincy Market is a bustling marketplace filled with food stalls, drinks, and souvenir shops. It’s the perfect place to grab a quick bite, whether you’re craving something classic like clam chowder or want to try something more adventurous like Korean Hot Cheeto fried cheese on a stick! We also grabbed boba tea while browsing the shops. It’s a great place to wander and sample fun eats from all over.
Paul Revere’s House
Located in the North End, Paul Revere’s House is the oldest remaining structure in downtown Boston, dating back to the late 1600s. Stepping inside feels like traveling back in time as you learn more about this legendary figure and his role in American history.
Explore Boston’s Freedom Trail
A classic! Even if you’re not a history buff, walking the Freedom Trail is a fun way to explore the city. The trail is a 2.5-mile-long red brick path that guides you through 16 historic sites, from Boston Common to the North End. The North End is a great place to stop for a bite to eat, especially if you’re craving Italian food (don’t miss Mike’s Pastry for their famous cannoli).
Take a Charles River Cruise
For a relaxing way to see the city, consider taking a Charles River Cruise. It offers a unique perspective of Boston’s skyline, especially during fall when the foliage lights up along the riverbanks. Perfect for an autumn afternoon, this peaceful escape from the hustle and bustle allows you to take in beautiful views without breaking a sweat.
Visit the Boston Public Garden
Boston’s Public Garden is a must-visit in fall. The changing leaves, crisp air, and swan boats (yes, they still run in October!) make for an idyllic afternoon stroll. Don’t forget to snap a photo at the iconic Make Way for Ducklings statues, especially if you’re visiting with family or friends who love children’s classics.
Visit the Museum of Science
If you’re into science and interactive exhibits, the Museum of Science is a great stop, especially if you’re visiting with family. They have a planetarium, a variety of exhibits, and even live animal presentations. It’s a fun and educational break from all the walking, and there’s something for everyone to enjoy.
Go to a Pub and Watch a Sports Game
Now, we unfortunately did not get the chance to do this because my sister was not 21 at the time. However, it seemed like EVERYONE in Boston was out watching football on Sunday! And Saturday for that matter! I remember seeing bars and pubs full of people drinking beer and having fun. I’d definitely recommend taking a break from all that walking you will be doing and enjoy a cold one while watching your team play at a pub in Boston. Also, I don’t think you can get more Boston than sitting in a pub, with a beer, watching a sports game. I watched the movie Good Will Hunting before my trip, and oh my gosh it was such a good movie and definitely got me in the mood for exploring Boston. So many scenes in diners and pubs. I snapped a photo of a cool pub while I was walking! It looks like it’s called The Bell in Hand Tavern. You should check it out, and let me know how it is!! 😆
Take a Day Trip to Plymouth Rock
If you have extra time, consider a short day trip to see Plymouth Rock, located about 45 minutes south of Boston. This iconic historical landmark marks the spot where the Pilgrims are said to have landed in 1620. While the rock itself may be smaller than expected, the surrounding area offers beautiful views of Plymouth Harbor and additional attractions like the Mayflower II and Plimoth Patuxet Museums, where you can dive deeper into early American history.
Day Trip to Salem
Looking for more fall magic and a spooky vibe? Salem is just 30 minutes away from Boston, making it the perfect day trip! Check out my Salem blog post for all the must-see spots, historical tours, and the best places to eat. Trust me, it’s worth the visit, especially in October!
Tips for Visiting Boston
Walk Everywhere
Boston is a highly walkable city, so take advantage of it! Many of the top attractions—like Boston Common, Beacon Hill, and the North End—are close to each other, making it easy to explore on foot.
Bring Comfortable Shoes
Pack sneakers or comfortable shoes because you’ll be doing a lot of walking. The cobblestone streets in some neighborhoods, like Beacon Hill, add to the charm but can be tough in uncomfortable footwear.
Pack a Rain Jacket
Boston weather can be unpredictable, especially in the fall, so bring a rain jacket. A light, waterproof layer will keep you dry and allow you to keep exploring even if it drizzles.
Use Public Transit (The “T”)
If you’d like to use public transportation,Boston’s subway system, the T, is an affordable way to get around the city. Grab a CharlieCard for discounted fares, and check schedules in advance—especially on weekends.
Dress in Layers
Fall weather can fluctuate a lot, so dress in layers. Chilly mornings can turn into warm afternoons, and you’ll want to stay comfortable throughout the day.
Book Popular Tours in Advance
If you plan to do popular tours like the Boston Tea Party Museum or historical walking tours, book in advance, especially in the fall when tourism spikes.
Watch for Street Performers
Keep an eye out for street performers, especially around Faneuil Hall and Boston Common. You might stumble upon musicians, magicians, or other performers, adding a fun surprise to your day!
I hope you have the most wonderful fall weekend in Boston!!! This is one of the coolest cities in my opinion with so much history, architecture, day trips, and things to explore. Safe travels. Xx
