What to Do and See on a Weekend Trip to Boston in the Fall

When I got the opportunity to visit Boston for a weekend in the fall, I was already dreaming of the fall foliage and New England comfort food we would try. If you’re hoping to see peak fall foliage, I actually suggest visiting the second or third week of November. Nonetheless, fall is still a beautiful time to visit Boston. Our time in Boston was very short, but I thoroughly enjoyed everything we did, and I am so excited to share my must-do tips with you for what you should see and do.

What to Do on a Fall Weekend in Boston

Walk the Freedom Trail

The Freedom Trail is a 2.5-mile path going through downtown Boston. This trail passes 16 significant historic sites. I’ve heard the trail is quite easy to navigate, but I must be honest and say we lost our way at the beginning of the trail. We made it to two historical sites and then could not see where the trail was leading. Despite our easy access to GPS and guides on our phones, we were still unable to figure it out. We ended up going down a few streets and entering some shops. Eventually, we realized we had somehow made our way back onto the Freedom Trail! We took it to the Quincy Market, but that’s as far as we went. If you’re able to navigate better than us, I recommend doing it! I think we were just really low on sleep after a full night of driving.

Quincy Market and Cheers Shop/Bar

The Freedom Trail brings you to Quincy Market, where you can find all kinds of food! Since we had already eaten, we did not grab food anywhere. But I was very tempted by all the enticing foods and smells.

There is also a store called Cheers Gift Shop, which sells memorabilia from the show Cheers. I have personally never seen this show, but I know my dad is obsessed with it. I decided to buy his Christmas gift here, eventually choosing a beer cup for him. When you go back up the stairs, you also see the entrance to the actual bar Cheers and cardboard cutouts of characters from the show. I had to grab a photo to show my dad.

Brunch at Tatte Bakery & Café

One place our friend in Boston said we had to eat at while we were there in the fall was Tatte Bakery and Café. This adorable café has multiple locations throughout Boston. However, the location we chose to eat at, which was located close to Newbury Street, was crazy busy. We ordered food but were not able to get a table. So, we took it to-go and decided to eat it on the steps of a church downtown, which worked out just fine. When traveling, you have to be able to roll with the punches! The food was delicious. I highly recommend visiting one of the many locations for brunch. Hopefully, you’ll have more luck snagging a table than we did.

Shopping on Newbury Street and Ice Cream at Emack & Bolios

No weekend trip to Boston in the fall is complete until you’ve shopped on Newbury Street. There is a good mix of major retail stores, smaller businesses, and restaurants. You can spend a good amount of time here, as there are several blocks full of stores. Our friend took us to the best ice cream shop called Emack & Bolios. It is nothing special to look at from the outside, but I must tell you I would travel back to Boston just to have a taste of this ice cream again. It is a hidden gem! This ice cream shop puts cereal on its cones. The best way to describe it is to have you look at my photo below. I got the lucky charms cone with ice cream. SO GOOD.

Beacon Hill and Acorn Street

If you’re looking to explore a more upscale part of Boston, Beacon Hill is the place to visit. Acorn Street was the epitome of autumn. This cobblestone street was coated with the prettiest fall leaves when we visited! I had a fun time taking photos here, as did other tourists. As I always say, just be respectful of those who live in the houses. Do not be overly obnoxious or loud, and do not take too many photos directly in front of their homes. There are other cute streets to explore in this area as well, so make sure you do not just do Acorn Street and leave. Spend an hour or two exploring this area and admiring the fall décor outside most of the homes in this area.

While all these activities would be fun any time of the year, I think they are most enjoyable during a fall weekend in Boston. I absolutely loved the scenery around the city and all the decorations that were still left up from Halloween. Next time I visit, I will definitely have to try some New England seafood! I’m new to the seafood game, so any recommendations of places to have good seafood in Boston are highly welcomed.