A First Timers Guide to Boston In The Fall

Are you planning a trip to Boston this fall? It’s incredibly beautiful during the Autumn months, and I’ve got your travel guide with the best places to go and things to do while you’re there. From shopping, restaurants, and ghost tours, this post will go over everything you need to know about visiting Boston In The Fall.

A First Timers Guide to Boston In The Fall

Where to fly into?

The Boston Logan Airport is very easy to navigate! Since we came from Maine we drove into Boston (in rush hour… definitely don’t recommend that), and flew out of Boston.

Newburyport, Massachusetts

We started our trip in Newburyport, Massachusetts. This town is a perfect New England town. It has rows of cute brick buildings and cobblestone streets. There were large open areas and the intersection of different streets meant there was always something new to see around every corner. Getting to Newburyport was charming in itself. The road winds past perfectly maintained New England homes. They had a lot of cute restaurants and shops to explore plus a beautiful park on the water.

Boston, Massachusetts

We drove into Boston, Massachusetts. Well, crawled really. Up until Boston, there was little to no traffic the whole way down the coast of Maine and New Hampshire. The last 5 miles took almost an hour to get through. It was excruciating. However, once in Boston, walking and the Subway/ Train system make it extremely easy to get around. You really don’t need a car in Boston, or if you plan on going to Salem! Transportation is easy in town.

Haunted Pub Crawl Tour in Boston in the Fall

The first night in Boston we went to a Haunted Pub Crawl tour. This was a fun way to shake off the day and see a few of the historic sites of Downtown Boston. We booked it with Nightly Spirits and Lucy did a great job telling tales of the haunted city. The best place on the tour was the speakeasy inside the Carry Nation Bar. Although it was more a restaurant than a Speakeasy, it was a definite vibe with great cocktails.

We stayed at Revere, as in Paul Revere. The hotel was centrally located and had easy access to the train lines and trolley stops. It is also close to the Boston Commons and has tons of great places to get a bite to eat. Our two favorites while we were there were Tatte and The Thinking Cup. The Tatte has multiple locations across the city, and although it is a little pricey the food is delicious. The Thinking Cup was less expensive but offered a warm inviting environment. The food there was excellent and made us feel comfortable when the Nor’easter storm brought the rain in.

Downtown Boston in the Fall

Boston is similar to New York in that there is so much history packed into such a small area! Unfortunately, it rained during our entire day in Boston but it was kind of fun!

We opted for the Hop On Hop Off Boston Trolly tour to help us get an overview of the area. Although the tour was VERY different than the Salem tour, it did get us to a few new areas throughout the day. All in all, it costs less than taking multiple Ubers to get around the city. We had 3 tour guides and one was incredible! What’s nice is you can hop off if you don’t like one guide and grab the next trolley to see if the new guide is any better.

Our favorite areas of Boston were Beacon Hill and The Waterfront towards the North End.

It was pouring so we stopped into Quincy Market. This was a massive food hall and shopping mall and is surrounded by modern stores like Sephora, Loft, and Urban Outfitters. If you head across Atlantic Ave, there is Christopher Columbus Park and The Greenway. The Greenway is a series of parks that stretch down Atlantic Ave.

At the very end, there was the coolest Merry-go-Round, except the traditional animals were exchanged for native Boston animals.

We had lunch after Quincy Market at the Green Dragon Tavern. The Green Dragon Tavern was considered to be the headquarters of the American Revolution. This is where Samuel Adams and the Sons of Liberty frequently met leading up to the revolution.

Beacon Hill

The bus tour traveled around the North End and over to Beacon Hill. Beacon Hill is also known as Antique Row. In fact, The buildings on Charles Street in Beacon Hill are federally protected historic sites. This means that they can never change what the outside of the buildings looks like. It almost feels like you stepped onto a movie set. There are so many shops and stores to pop in and out of and of course, a Tatte Barkery to get a coffee to keep you going. One of the more interesting shops we went in was Beacon Hill Books & Cafe. The Cafe is downstairs and to get to it you have to walk down this tiny corridor in the building. It felt very much like a scene from Harry Potter. The bookstore is above the cafe. It was so fun exploring these little gems.

I’m usually not a huge antique or fine china person but Elegant Findings Antiques in Beacon Hill changed me! They had the most incredible collection of stunning china I have ever seen! This is a must-see!! The owners are so sweet too- they’re an older couple and seem to truly love what they do. They taught me a lot about different types of china and where it’s from, what makes each piece special, etc. Such a wonderful store!

We finished our trip by having dinner at the famous Union Oyster House! The Union Oyster House is one of the oldest restaurants in the US. Many famous people have passed through its doors, one of the most notable being John F Kennedy. He frequented the restaurant so much that he had his own table, #18. We made a reservation and I’m glad we did! They were packed!

We flew out of the Boston Logan Airport and it was an easy, drama-free experience. We had the best time in New England and can’t wait to go back!