Fall in Boston: What to Do for a Long Weekend

Explore this New England city during its peak.

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Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Photo By: Molly Miller

Boston is the ideal fall getaway. Flights are cheaper, and its quaint charm will appeal to every kind of traveler.

Maybe it's the picturesque location, situated right on the Charles River and Atlantic Ocean. Maybe it's the old world cobblestone streets and rich history. Maybe it's the pleasant temperatures: not too hot, not too cold. Or, maybe, it's the impossibly fresh lobster and shellfish. For me, all of the aforementioned reasons (and more) set Boston apart as the perfect long weekend destination.


Clearly, I fell head-over-heels in love for Boston. Here are a few reasons you will, too.

It's Walkable

Boston has beautiful fall weather, so take advantage of it!

But, public transportation is also very easy to use. The T, as locals call it, will quickly take you wherever you want to go in the city. I stayed with my friend in Arlington, and it took about 30 minutes to get downtown. Once you're in the city center, here are a few walking routes I recommend.

Route 1

Follow the Freedom Trail. This brick path will take you past every notable historical site in the city, including Bunker Hill, Paul Revere's house and the Old North Church. Start at Bunker Hill, working your way down across the Charles River. (Tip: If your legs need a break from climbing 294 steps at Bunker Hill, take a ferry to Long Wharf for fantastic views of the Boston skyline.) Follow the trail to the Old North Church, down to Paul Revere's house in the Italian district, through Quincy Market to the Old South Meeting House and, finally, to the Boston Common. Cheers fans will be happy to know that the iconic bar is located nearby on Beacon Street.

Route 2

Start at the intersection of Newbury Street and Massachusetts Avenue for shopping and sightseeing. Boylston Street (one block over from Newbury) takes you past the Boston Library, Boston Marathon Finish Line and Trinity Church. Both Boylston and Newbury run into the Public Garden, where weeping willow trees dance in the wind over a pond. After a stroll through the Public Garden, head into Beacon Hill via Charles Street for a taste of old Boston.

Route 3

Explore the burgeoning art district near the South End, SoWa Art + Design District. Here, you'll find open markets, hip restaurants, art galleries and festivals. Then make your way through Chinatown, towards the Boston Tea Party Ship and Museum, and on to Harpoon Brewery to close out the night.

There's Something for Everyone

For nerds, Cambridge houses the esteemed universities MIT and Harvard. Explore the campuses, libraries, bookstores and museums in the area for a day of educational fun. You'll get a real taste of campus-life in the fall when school is in session.

Shopping fanatics will love Newbury and Boylston streets for their high-low mix of stores. Here, you'll find everything from Madewell and H&M to Balenciaga and Chanel. It's the perfect spot to get all of your fall (and holiday!) shopping done.

Foodies and beer geeks can take advantage of Boston's many breweries, like local favorite, Trillium, and inventive restaurants. If restaurant and brewery hopping doesn't keep you busy, attend one of Boston's many food festivals that take place in September and October, like the Copenhagen Beer Festival.

Outdoor enthusiasts can find enjoyment in the urban jungle thanks to the Charles River. Rent a kayak to see Boston by boat or borrow a bike to explore the city's many greenways. Bostonians are very active, so you won't feel out of place taking a jog through its neighborhoods.

Artsy types will feel right at home in SoWa, with its galleries, artisan markets, shared creative spaces and fresh, organic food options. The Opera House, Museum of Fine Arts and Institute of Contemporary Art all warrant a visit. Plus, tons of new exhibits debut at museums in the fall.

Families will enjoy the Museum of Science or New England Aquarium. Grab ice cream afterward near the Greenway Carousel, then saunter over to Quincy Market to see street performers and shop from local vendors. There's also an adorable tribute to the famed children's book "Make Way for Ducklings" in the Public Garden.

In addition to the Freedom Trail, history geeks should also visit the Boston Library, USS Constitution Museum, the Isabella Stewart Gardner Museum and Old State House. These usually packed tourist spots will be almost empty in the fall.

It's Gorgeous

Between the cobblestone streets, historic sights, numerous parks, waterfront views and brownstones with luscious planter boxes, Boston's beauty can't be denied. If you go at the perfect time, you'll catch stunning fall foliage, too.

For beautiful river views, the Esplanade can't be missed. Situated just a few blocks from the Boston Common and Boylston Street, this public park is a popular spot for locals during summer and fall. Rent a sailboat for a day on the river or sit back and watch them sail by, coffee in hand from the Charles River bistro.

You'll Eat Well

Gotta fuel up for the long winter, right?

Mario Batali's Eataly is a MUST. This marketplace-slash-eatery offers fresh seafood, house-made cheeses, a meat counter, wine shop, local produce and 14 spots to grab a bite. Plan to spend at least two hours here.

In Cambridge, try the acclaimed tapas restaurant Little Donkey, the Border Cafe for a fun atmosphere with Tex-Mex and Cajun food, and grab a cannoli from famed Mike's Pastry.

Like seemingly every other major city in the U.S., Boston loves brunch. If you're staying near Arlington (like I did), Rosebud Diner serves up homemade doughnuts and incredible eggs benedict. In the city center, Beehive is a local favorite as well as Abe & Louie's or The Gallows in the South End.

Pizza and seafood reign supreme here. Check out popular seafood spot Neptune Oyster for mouth-watering lobster rolls and, of course, oysters, Legal Sea Foods for an upscale experience or Yankee Lobster Co. for seaside views. Regina Pizzeria, Za, Area Four, Ernesto's or Picco serve up delicious slices of pie, all with their own twist.

For Asian fare, try the Thelonius Monkfish in Cambridge or Gourmet Dumpling House, Hei La Moon and Shojo Restaurant in Chinatown.

Day Trips Are Very Doable

Small, picturesque coastal towns lie less than two hours away from the bustling city. Halibut Point in Rockport is a lovely place to spend the afternoon. Pack a picnic and watch the waves crash against the craggy shore. Then, grab dinner and browse local shops in idyllic Rockport.

Newport, Newburyport, Cranes Beach, Portsmouth and Martha's Vineyard also make for great overnight stays or day trips. Even better? Tourism dies down in the fall, so, you'll virtually have these towns to yourself.

And don't forget about apple picking and pumpkin patch visits! Massachusetts is ripe with apple orchards, vineyards and pumpkin patches.

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