Charming neighborhoods, cobblestone streets, harbor views, and quick day trips to beautiful destinations — Boston really does have it all, and one of the best times to visit the historical city is right now!
That’s right; while Boston is a winner in all seasons, fall is a magical time in Beantown. The trees begin to change color, and the air becomes crisp, making for the most picturesque cityscapes in the U.S.
And if Bostonians are one thing — it’s spirited.
The city’s people are extremely proud of their sports culture but also know how to celebrate a season or two. If you visit in the fall, expect to see pumpkins… everywhere!
Decor Done Right
If you’re familiar with Boston, then you’ve heard of Beacon Hill, one of the most charming neighborhoods in the city; think: narrow alleyways, towering brownstones, and decorative stoops.
Each year, residents go above and beyond in a stoop competition in the fall. Last year, the city saw an entire house inspired by the Harry Potter movies, graveyards, and more- it’s really something not to be missed if you’re here.
Another neighborhood that goes above and beyond is the South End. If you take a stroll down any of the side streets in the fall, you’ll feel as though you’ve taken a day trip to Disney!
Hundreds of tourists visit each year to catch a glimpse of the spooky show. One house in particular is known for its politically-themed Halloween decor if you need a good laugh!
So Many Day Trips
If you’re worried about what to do when you visit a new place… don’t be. In a prime location on the East Coast, Boston makes it easy to take an abundance of day trips from the city.
Short, long, overnight: no matter how much time you’re spending here, there’s something for you. Well connected to other U.S. States and MA towns, Boston’s public transportation is pretty easy to navigate for newbies.
- Trips under an hour or so → If you want to keep it short and simple, there’s plenty to see. Take a quick boat trip to Provincetown, venture over to spooky Salem, or hop on the commuter rail to Newburyport, Rockport, or Gloucester.
- Longer day trips → Rent a car and drive through the Berkshires to see some of the best foliage in the country or pop over to New Hampshire for the day. It’s even possible to drive or take a train to Cape Cod, and then sail over to Nantucket or Martha’s Vineyard.
Boston Knows How To Do Oktoberfest
I did say Boston was a spirited city, and the fall really brings this out of people. The entire city celebrates Oktoberfest, almost to the extent Germans do!
This year alone, there are over 5 celebrations around Boston. Breweries decorated, people donning lederhosen and dirndls, oompah bands, and free-flowing beer: you’re sure to have a good time at any one of these!
For a day of family fun, Harvard Square celebrates its legendary Oktoberfest celebration each year with a music parade, sidewalk sales, and an array of food vendors and beer gardens.
Here’s a link to some of this year’s events!
Beautiful Hotels
Looking to stay directly in the city? Luckily for you, there are plenty of hotels that also offer some of the best views around Boston. Small boutique options facing tree-lined streets and luxurious towers with rooftop bars: you’re bound to enjoy some good foliage spotting.
So, I’ve convinced you to stay in Beacon Hill? The Liberty is one of the city’s most beautiful hotels with an eerie past. A former prison with an eye-catching lobby area, the hotel is on the outskirts of Beacon Hill and across from the Charles River — ideal for leaf-peeping!
The city’s newest opening has stirred some excitement. The first Raffles Hotel in the U.S. has found its home in Boston! With a sky-lounge, spa, and speakeasy, Raffles is a new hotspot in the Copley area (aka a foliage haven near Newbury Street!)
More hotels and Boston tips here!
Prime Location
This one doesn’t need much explanation. As a central hub for travel, flights to Boston are usually pretty affordable if you get them early enough!
Flights in October can be found from Chicago to Boston for under $100 roundtrip, and from San Francisco, they’re as low as $220 roundtrip. As one of the busiest times of the year in the city, these flight prices are extremely reasonable to visit.
