Guide to a Fall Weekend in Boston, MA
New England does fall best.
I’ve been wanting to take more advantage of my proximity to so many amazing cities and towns on the East Coast that are in driving distance and Boston was high on my list.
There’s really nothing like New England in the fall with so many towns that embody the essence of the season (Salem, MA, Woodstock, VT, Portsmouth, NH) but Boston was still my number one. It’s about a five hour drive from the NJ/NYC area, but you can also take an Amtrak. There’s plenty of hotel and Airbnb options in whatever area you’re looking to stay in (we chose Downtown Crossing for its proximity to the Back Bay/Boston Common area).
Here’s a few of the places I’d recommend for eating, drinking and doing:
Eating/Drinking:
Burro Bar - We ate here for dinner one night (the South End one) and had some killer Mexican food. I loved the Short Rib ‘Double Stack’ and Crispy Chicken tacos. You could easily walk from downtown or take a quick Uber.
Tatte - This is a given as there are Tattes everywhere in Boston, but it’s definitely worth stopping into for coffee or a bite. Their pistachio latte is to die for (I liked it iced). They’re only in Massachusetts and the D.C. area so it’s a must if you’re visiting Boston.
Thinking Cup - We stopped into their Back Bay location for a quick bite before doing some strolling along Newbury Street. It looks small on the outside but there’s tons of seating and great for grabbing a cup of coffee and a pastry or breakfast sandwich (the breakfast burrito was great.
Haley.Henry Wine Bar - We stumbled upon this wine bar after dinner one night since it was close to where we were staying. They’re a natural/small production wine bar and I also learned that they were a 2024 James Beard Semi-Finalist for “Outstanding Wine Program.” We walked in and grabbed a spot at the bar but if you’re going to eat there too, I recommend a reservation.
Yvonne’s - This place came highly recommended as a dinner spot but we popped in for some pre-dinner drinks. It’s super vibey/has a speakeasy/underground feel to it that’s really cool.
Coppa - This might’ve been the highlight of our trip when it comes to food. It’s tucked away in South End and is small and cozy. It’s Italian so think sharable pastas, pizzas and apps (it’s helmed by a JBF-winning chef). We got the Burrata, Broccolini (made with Pumpkin Romesco which was incredible) and a few pasta dishes. I paired my Spaghetti Carbonara with a glass of Chianti (my go-to).
Flour Bakery - Similar to Tatte, there’s a couple of Flour locations around Boston. We went to the Harvard Square one for a quick bite and coffee before checking out the university.
Doing:
Beacon Hill - The Beacon Hill area was a highlight for me - think cobblestone streets, independent shops and plenty of photo opps (especially when all decorated for Halloween). Acorn Street is one the most photographed streets in the U.S., and definitely pop into Beacon Hill Books & Cafe.
Newbury Street - Think the SoHo New York of Boston. You’ll find a stretch of high-end shops, restaurants and runs right into Boston Common.
Boston Public Library - We stopped in here to check it out as it’s right off Newbury Street. It’s the third largest public library in the U.S. and has some cool architecture inside.
Marblehead - Not technically in Boston, but it’s about a 40-minute drive north of the city. It’s a cute coastal town with a main street and some restaurants along the water. I’m sure it’s crazy in the peak of summer so it was nice to see it in the off season. We grabbed a drink and a bite from The Landing Restaurant for some scenic views of the coast.
Harvard Square - On our way out we wanted to see Harvard so we headed over to Cambridge and walked around Harvard Square and the university. I love a college that has a fun town surrounding it, and there are plenty of things to do in Cambridge (you could spend a full day/night there).
Harvard Museum of Natural History - I love any kind of natural history museum and they were doing free admission on this particular day (otherwise it’s about $15 for adults) so we spent an hour or so roaming the museum. They had a new Sea Monsters exhibit which I loved, and a great activity if it’s chilly or cold outside (which it was for us).
