If you’re looking for the perfect weekend fall getaway, consider a trip to Boston. It’s got history, beautiful sites, quaint neighborhoods, culture and excellent food! We spent three full days and were able to pack in a lot on top of enjoying some downtime. Boston is a colonial town which was first settled in 1630 date, so the city is very walkable. It’s the perfect spot to visit on a long weekend especially with all the beautiful fall colors. You’ll get to see a lot during a weekend getaway because there is so much in such a small vicinity!
We booked our trip less than a month before our travels. We didn’t do a whole lot of research before booking since the flight was cheap and we had a flight credit we needed to use.
During our stay at the end of October, it wasn’t quite the peek of the fall colors but we did see a lot of trees that had changed to brilliant colors during our trip. The weather was in the 30s – 50s and man was it cold. It rained during our stay which cut into some of our plans. We still were able to see and do a lot and we really enjoyed our time. Boston is the perfect weekend getaway and I highly recommend visiting! Read on for information on where we stayed, how to get around, sights to see, things to do and places to eat in Boston.
Where We Stayed:
From what we read online the Back Bay neighborhood is good for the younger crowd, lots of action, restaurants, walkable and not to mention, very pretty.
We really liked the Back Bay neighborhood and were able to walk to a lot of things in the surrounding area. It was centrally located to a lot of the sights we wanted to see and at times we only had a quick Uber/Lyft ride to our destination.
Airbnb’s were a lot cheaper than the hotels we were seeing. Boston hotels were pretty pricey and the Airbnb we stayed at was quaint. If you have more time to plan, definitely check out hotels in advance or look for a good deal. Airbnb’s are a great alternative and it was fun staying in a neighborhood.
- Walking: Boston is known as a walkable city. We did a lot of walking and there’s a lot of things that are within close proximity within each other. Prepare for a lot of walking in Boston.
- The T: Boston’s form of public transportation, the T, is comprised of buses, trains and even boats. A one-week pass costs about $20 which will give you access to buses and trains. This is really affordable and you’ll find bus stops and trains everywhere. We thought about getting a pass but ended up walking everywhere and using Uber & Lyft.
- Uber & Lyft: Both were decently priced. They weren’t as cheap as it would have been to get a week pass for the T, but we were sick and Uber & Lyft were very convenient especially with ride share. We opted to use Uber & Lyft between greater distances. We didn’t mind paying a little extra money to get to our destinations a little quicker.
Sights to See:
Boston is brimming with beautiful sights all over the city! The city is walkable with historic sites and buildings all over, with a lot being near one another. I loved the fact that there was so much to see and a lot of it didn’t cost a penny. Fall is especially a beautiful time of year to visit with all the autumnal colors. Below are free must-see sights in Boston that you should be sure to visit!
When we first arrived we were dropped off at Copley Square. It has a quaint park where a Farmers Market was being held. The Farmers Market is held on Tuesdays and Fridays and runs from early May through late November. Situated around the Square are the Boston Public Library, Old South Church and Trinity Church among other buildings. The area is brimming with beautiful architecture and it’s the perfect place for an afternoon stroll.
Founded in 1634, Boston Common is the oldest city park in the United States. Rich with history and beautiful sights, it’s a must see during a visit to Boston. During the park’s long history it was used for cow grazing, hangings, assembling of Colonial troops during the Revolution and much more. George Washington, John Adams and General Lafayette convened in the park to celebrate America’s independence from Great Britain. It’s a beautiful park to walk around and enjoy. The Freedom Trail begins in the park, more on that below.
Faneuil Hall Marketplace
Faneuil Hall was built in 1742 and was not only a marketplace but it also was a place where people gathered for discussions and debate. Colonists gathered here to protest the Sugar Act in 1764 and it’s where they established the philosophy of “no taxation without representation”. The Golden Grasshopper sitting atop the building has been there since the building’s creation. The stomach of the grasshopper houses a time capsule that was originally added in 1761. The shops in the marketplace are rather touristy, but the outside architecture is beautiful and the history makes it worth a visit.
Faneuil Hall expanded in the early 1800s to include Quincy Market. The market houses food and retail vendors. It’s fun to look at and walk around the shops and vendors. We opted to not eat at any of the vendors because the food looked so-so. We didn’t explore the surrounding buildings and shops, but there’s even more to explore in the marketplace and perhaps we missed out on some even better restaurants and vendors. Given the history of the area and the architecture, I definitely recommend checking it out.
We had lunch in Cambridge near Harvard Square. After lunch we walked around part of the campus. It was especially beautiful in fall. Harvard is the oldest University in the United States and one of the most prestigious in the world. The campus has stunning architecture and it has a few museums that are open to the public. You can join a tour lead by students for free. This tour departs from the Harvard Information Center, in the Smith Campus Center. We opted to walk around the campus on our own. You can also purchase a map for a self-guided tour.
Beacon Hill Neighborhood
What can I say? Beacon Hill is GORGEOUS! I went to college in Richmond, Virginia and we had rowhouses like those in Beacon Hill, it felt very nostalgic to me, so I was especially fond of the neighborhood. The neighborhood is incredibly charming and especially beautiful during the fall with the changing colors of the leaves and adorably fall-decor adorned homes. The neighborhood is historic and you’ll find lovely homes lining the brick sidewalks and occasional cobblestone street. Homes in Beacon Hill began being built in the 1800s. Beacon Hill is an absolute must-see in my opinion. Be sure to check out Acorn Street, Chestnut Street, Louisburg Square and some of the cute stores on Charles Street.
Boston Public Library
Truly another must-see sight in Boston is the Boston Public Library. Founded in 1848, it was the first large free municipal library in the U.S. The building on Copley Square was built in 1895. The art and architecture are very grand. You’ll find cards explaining the art throughout the building. The outdoor courtyard is very charming and is the perfect place to enjoy coffee or tea with your companion.
Things To Do:
The Freedom Trail
We really loved this tour. It was only about $15 and lasted an hour and a half. The tour covered a lot of sites that were close to one another and the guide was very knowledgable. There are a few different tours you can take that highlight various sites. We took the most popular tour which allowed us to view over 11 historic sites. The tour we went on runs hourly from 11 am – 4 pm daily. The tour started at the Boston Common Visitor Information Center and ended at Faneuil Hall. The sites we saw included: The tour covered Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel & King’s Chapel Burying Ground, Boston Latin School site/Benjamin Franklin statue, Old Corner Bookstore, Old South Meeting House, Old State House, Boston Massacre site and Faneuil Hall. I definitely recommend the tour, it was a great price point and it covers a lot!
Boston Public Market
There were tons of vendors at the Boston Public Market. It was fun exploring the different vendors and food offerings. The indoor market is great for meandering and has a lot to offer food-wise. It’s worth taking a stroll through. There were many great smells and sights in the market.
Boston Tea Party Ships & Museum
This was not only a tour, but there were also delightful historical interpreters who made the experience very entertaining. We were given a history lesson throughout, toured a restored 18th Century sailing vessel and saw historic artifacts. After the tour we enjoyed hot cider at the museum’s tea room. The Freedom Trail walking tour was by far my favorite tour, but this tour was entertaining and educational and I would recommend it.
Where We Ate:
On our first day we had lunch at Shojo in Chinatown. It was a trendy restaurant that had good reviews on Google which drove our decision to dine there. The restaurant was packed which seemed promising, but we ultimately felt the ratings had been overhyped. The service wasn’t good and we thought the food was so-so. It was a fun, hip atmosphere. It could be worth a try, but we both felt we’ve had better meals and service elsewhere.
This restaurant was nestled in the North End which is known for its great Italian restaurants. When we first ventured up, we were afraid we had gotten incorrect directions as the block had no other restaurants or shops. You take a small flight of steps down to the entrance of the restaurant. Upon entrance, it’s small, packed, dimly lit and has a warm glow from the lighting and red interior. The restaurant was incredibly charming and the food was phenomenal! I highly recommend this restaurant! Definitely try to get a reservation beforehand, they take minimal walk-ins and we were lucky that we got a table. It’s very romantic and it was by far our favorite meal that we had! The restaurant isn’t exclusive to couples, we saw a few groups of friends that were enjoying the restaurant just as much!
The Hourly Oyster House
This was yet another great restaurant we dined at. The Hourly Oyster House had a lovely interior and we enjoyed a nice meal. The restaurant is in Cambridge and it has a lot of Seafood options. I’d definitely recommend it for the food and atmosphere!
Since we were sick during our trip, we didn’t feel like full sit down meals a couple of evenings. I discovered by CHLOE. on Instagram and was very excited to see one in Boston! We gave it a try one evening and both Guayo and I overall enjoyed our meal. They are strictly a vegan restaurant. I had avocado pesto pasta which I loved and Guayo had a mushroom burger which he thought was pretty good. The restaurant is very trendy and has pretty healthy and quick meal options. If you’re looking for something fast, healthy and delicious, this is a restaurant you should try!
I’ve been a fan of Georgetown Cupcake for years! Their original location is in Georgetown in Washington D.C., hence the name, but they’ve expanded to other cities. Their cupcakes are phenomenal and well worth a visit! My boyfriend felt they lived up to my hype and he’s not majorly in to sweets. Over the years I’ve gotten my family hooked on them as well. The owners had their own TV show on TLC and have cookbooks out which I own. I regularly make cupcakes from their book and they are always a hit!
Tatte Bakery & Café
This was by far my favorite spot we ate at (tied with Grotto)! Tatte has over ten locations, six of which are in Boston. We went twice to the café in Back Bay and both times it was pretty packed, especially on the weekend! The food was excellent; the first time we went, I had a croissant sandwich and Guayo had shakshuka. Our second time around, I had a mozzarella sandwich with tomatoes and pesto and Guayo had a farro bowl that was filled with fresh veggies. Both of us got pastries to go, a brownie for me and a pistachio croissant for Guayo – they were excellent! Tatte Bakery & Café is a must when you’re in Boston! The food and atmosphere are delightful and I will go back in a heartbeat the next time I’m in Boston.
Legal Sea Foods
Our last stop was Legal Sea Foods before we left. At that point I didn’t have much of an appetite, but if you know me, you’ll know I always have room for something sweet..! My dad has visited Boston many times over the years and has always raved about Legal Sea Foods. They have numerous locations so they’re pretty accessible. Guayo had oysters which he said were great! I opted for Boston Cream Pie which I couldn’t leave Boston without trying! It’s not my number one favorite dessert, but it was really good and definitely worth a try when you’re in Boston.
- Be prepared for the weather: Bring lots of layers. Also make sure you’re prepared for the rain. Rain in the fall on the East Coast is pretty common.
- Have some indoor activities planned in the event that the weather is less than stellar.
- Group your activities by location. Even with the city being walkable you can easily walk 30 minutes between destinations. We tried to plan accordingly and took Lyft and Uber rides here and there.
- Check out local events during the time you’re visiting. The Boston Calendar lists endless options!
We really loved Boston! Between the history, architecture, beautiful public spaces and great food, it’s the perfect spot for a weekend getaway! It doesn’t require a ton of planning in advance and it’s chock-full of things to do and sights to see.
Have you ever been to Boston? What are some of your must-sees and favorite places to eat? If you haven’t been to Boston, where is your favorite spot for a weekend getaway?