A Local’s Guide to a Weekend in Boston

A Local’s Guide to a Weekend in Boston

  • Danielle D’Ambrosio, Esq.
  • 08/23/22

Boston is a fascinating city. With iconic parks, a beautiful harbor, an amazing dining scene, and a plethora of activities and attractions to suit any taste, Boston really does have it all.
In a city like this, how do you choose to spend your weekend? Truth is, there’s so much to do you’ll most likely want to keep coming back to visit—and maybe to stay! If so, there are some amazing townhomes with incredible water views on the Boston Waterfront.
From our local perspective, here are a few things you should add to your weekend itinerary of things to see and do in Boston.

All the best ways to spend a weekend in Boston

Old Ironsides

The gem of Boston Harbor is the USS Constitution, the world's oldest commissioned warship, which means that it has never been removed from active service. Open to the public every day except Mondays, the free admission grants you access to the top three decks with crew members on hand to answer your questions. A passport or photo ID is required to board the ship. After your self-guided tour, visit the small museum near the ship. Note that the museum and ship are run separately, and museum admission is a suggested donation of $10-15 per adult and $5-10 per child. However, you can gain free admission through your public library.
However you decide to spend time on the USS Constitution and its adjacent museum, this is a unique opportunity to see a fascinating part of naval history right in Boston Harbor.

Shop til you drop

Boston is a great shopping destination, but if you’re looking for something truly out of the ordinary, how about stepping into an upscale streetwear store behind a fake Snapple machine in the back of a deli? Bodega is the clothing equivalent of a speakeasy, so make sure you keep this unique shopping experience an open secret!
If you’re looking for your next great read, make a trip to Brattle Book Shop. Established in 1825, here you’ll find a plethora of used, antique, and rare books. When the weather is dry, the books spill out onto the lot next door, which is where you can peruse bargain finds and more contemporary gems. They also offer a “decorate with books” service to help give your home that used bookstore look we all love—the smell of old books, a hot cup of tea, and the knowledge of treasured stories all tucked within.

Enjoy lunch and more at the Cradle of Liberty

Centuries ago, American revolutionaries met at Faneuil Hall. Today, it’s Boston’s biggest market and an incredible place to get lunch, from small food stalls to quaint eateries and leading restaurants. A marketplace where you can enjoy truly New England delicacies such as lobster rolls, corn chowder, Boston baked beans, and so much more, Faneuil Hall Marketplace also has a museum, walking tours, and retail specialty carts where local artisans sell their wares.
Outside the marketplace, there are often street performers juggling, showing off magic tricks, doing acrobatics, and more. For another excellent lunch spot, visit the Quincy Market Food Colonnade, which features 30 different merchants.
You may find that the hardest decision to make is where to get a bite from first!

Go on a pub crawl

This is New England, after all, which means that the great British tradition of the pub crawl is alive and well in Boston. Put together one on our own with friends, or join a guide, who can retell the great importance of beer to the nation’s founding. Your guide will also help you discover fantastic local craft brews you can only find right here in Boston.
Boston is home to over 30 breweries, so however you decide to do a pub crawl, you’re bound to have a great time. The oldest brewpub in the city is the Cambridge Brewing Company, which was established in 1989. Boston is also the original home of Sam Adams, which offers brewery tours on Saturdays.

Take a break in iconic parks

Boston is home to a number of iconic parks. America’s first public botanical garden, the Boston Public Garden features Victorian-style architecture and elegant swan boats. Boston Common is the country’s first public park—it was built in 1634!—is an open space that’s great for picnics with ballfields and a skating rink during the winter. Over its long history, Boston Common has seen cows, victory gardens, public assemblies, and much more.
Located in the heart of Boston, Rose Kennedy Fitzgerald Greenway used to be Interstate 93 before it was transformed into a linear park that offers food trucks, live music, outdoor movies, public art, and a carousel where patrons can ride on moving statutes of local wildlife.
Make sure also to check out the Esplanade, which is part of the Charles River waterfront. Beloved by joggers and cyclists, it has a popular bandstand and is the locale of the city’s biggest Fourth of July party. You can also take part in numerous recreational activities, including sailing, kayaking, and windsurfing lessons.
A park that many visitors may miss (but deserves fanfare) is the James P. Kelleher Rose Garden, which is tucked away in the Back Bay Fens. Open every day from May through October, this charming garden feels like its own little secret, even though it’s not that far from Fenway Park!

Explore Beacon Hill

When you think about Boston, you’re probably thinking about Beacon Hill. This is where you’ll find redbrick mansions, cobblestone paths, and tree-lined streets. Take a walk through this neighborhood from the Common up to Louisburg Square and then down Acorn Street, and make sure to bring your camera! Beacon Hill is incredibly photogenic and offers fantastic opportunities for street photography.
If you have a bit more time, the Nichols House Museum offers a glimpse of what these rowhouses were like when they were built. You can also visit the first floor of the exclusive Boston Athenaeum for free or explore the private library using a day pass.

Franklin Park Zoo

Designed as part of Franklin Park in 1912, the Franklin Park Zoo originally did not charge admission until 1958, when it went through modernization. If you look north of the stadium, you can still see the old bear pits.
Today, this modern zoo is home to animals such as lions, gorillas, zebras, Brazilian cockroaches, African pygmy falcons, warthogs, and more. Make sure to also visit their petting zoo, where you come up close and personal with Nigerian dwarf goats and Poitou donkeys.

Appreciate local cuisine

Boston has an incredible dining scene alongside New England classics like chowder and clambakes. Our location on the coast grants us access to delightfully fresh seafood while in the north of the city, you can find fried clam shacks. Sometimes some of the best food comes from the smallest places!
Boston’s Irish history makes for some excellent Irish pubs, while Chinatown is filled with a variety of Cantonese, Mandarin, Japanese, and other regional delicacies. Head to the North End and visit Little Italy, where local gem Regina Pizzeria cook their pizzas in a brick oven that’s almost a century old.
Don’t forget to try the Commonwealth’s official dessert, the Boston cream pie. It may not be an actual pie, but who’s counting? Other classic Boston food includes frappes, which are what we call milkshakes (note that if you order a milkshake here, you’re going to get flavored milk), fried clams, Greek-style pizza (in terms of crust style, not flavor), and Peking ravioli, which are Chinese dumplings with an Italian twist.

The Mapparium

You’ve heard about The New York Daily News famous globe? Well, the Christian Science Monitor tried to go one better with their three-story-tall, inside-out stained glass globe, which is known as the Mapparium. In fact, it gives a more accurate image of what the Earth is like than the globe, and is also a whispering gallery.
Find the Mapparium at the Mary Baker Eddy Library, which is named after the founder of Christian Science and includes a research reading room and various exhibits.

Fenway Park

Whether you’re a baseball enthusiast or a casual fan, Fenway Park is America's most beloved park for a reason. In operations since 1912, you can take a tour of the field during off-games, but when the season is in play, catch a game at a ballpark that is as storied as the very sport.

Ready to move to Boston?

We hope you enjoy our local guide to what to see and do on a weekend in Boston. Don’t forget to bring walking shoes (or snow boots if you’re visiting in the winter)! And if Boston appeals so much that you’re considering making it your permanent landing place, The D'Ambrosio Group can help you find the perfect luxury home on the Waterfront or the North End.

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