How to Spend a Historic Weekend in Boston

With so much history and a revolutionary spirit that can be felt even today, I promise you’re going to love spending a weekend in Boston.

Ever since the city was settled back in 1630 by Puritans fleeing persecution in England, Boston has place a crucial role in not only the founding of the United States but also in defining American culture and ideals. Even as local Bostonians take pride in their foundations and landmarks, they strive to continue leading the way in a way our founding fathers would more than approve.

Whether you want to learn more about our country’s history, enjoy the outdoors, or dig into some classic New England cuisine, here are all the best ways to spend a weekend in Boston.

Where to Stay for Your Weekend in Boston

Located in a historic Renaissance Revival-style building inspired by the Palazzo della Cancelleria in Rome, there’s no better place to stay for your weekend than the beautiful Langham Hotel Boston.

Recently renovated, the Langham oozes modern sophistication and comfortable luxury.  With such a good spot in the heart of the city, you’ll be close to all the major attractions and restaurants for your weekend getaway.

Ideas for Your Weekend in Boston

With so many unique things to do in Boston, there’s really something for everyone. Whether you visit during those biting New England winters or come for the milder, sunny summers, you’re sure to fill up your weekend easily.

Enjoy the Charles River

At over 80-miles long, the Charles River comes to an end in Boston and, it’s safe to say it plays a huge part in the city’s culture. There are plenty of ways to enjoy the river if you’re coming in the warmer months, including a nice bike trail that will lead you by some of the city’s most famous universities.

The best, though, has to be on the water especially if via rowing. Home to the Head of Charles Regatta, which any former collegiate crew member will tell you is one of the most important races out there, this city is made for rowing. Don’t worry if it’s your first time, the Community Rowing Inc. offers up classes no matter your level or age.

Explore Beacon Hill

When you think of classic New England streets, nowhere is quite as picturesque as the half-square-mile Beacon Hill neighborhood behind the Massachusetts State House. As one of the oldest areas in the city, it’s full of Federal-style brick row homes and the narrow cobblestone streets are lit by old-fashioned gas lamps. Start at the gold-domed state capitol building and just give yourself an hour or so to wander through. If you’re here during the early spring season, be sure to stop at the Charles River Esplanade to see the cherry blossoms in bloom. And do not skip the Boston Athenaeum, possibly one of the most beautiful libraries in the country.

Follow the Freedom Trail

Considering you’re visiting one of the most historic places in the USA, you’d be missing out if you skipped any of the 16 sites along the 2.5-mile long Freedom Trail. Established by Bostonians in 1951, the trail leads to a number of significant landmarks that help tell the story of the American Revolution and how our country became, well, a country. Stop by places like the site of the Boston Massacre, where the war began, Old South Meeting House, where locals gathered before moving to the harbor for the Boston Tea Party, or the Bunker Hill Monument, where the first major battle was fought.

While you can do a self-guided tour along the trail, they also offer themed options like the African-American Patriots, Revolutionary Women, or Lantern tours.

Catch a game at Fenway Park

If you weekend in Boston falls during baseball season, it almost feels like a crime to miss the Red Sox play at Fenway Park. One of the oldest active ballparks in the country, it’s has been open since 1912 and is a historic monument all its own. Even if you can’t catch a game, they offer tours throughout the day where you can learn about legendary players who’ve called this place home and see just how much it’s meant to the city through the last century.

Trace your lineage one of the most expansive genealogical societies in the world

If you’re interested in your family tree even in the slightest bit, you’ve got to set aside some time to visit the New England Historic Genealogical Society (NEHGS). It’s been open since 1845 and currently holds eight floors of material for research. Get a head start on your tree with AmericanAncestors.com and then schedule a session to research in person. If you want extra help, you can even hire an expert for a one-on-one session.

Go on a tour around Roxbury

One of the oldest places in the U.S. Roxbury dates all the way back to 1630 when it was one of the first towns founded as part of the Massachusetts Bay Colony. During the 20th century, it became the heart of Black culture in Boston and continues to carry that legacy into the present day. You know you’ve got a place in history when both Martin Luther King Jr. AND Malcolm X have called you home at one point!

I highly recommend doing a tour with Live Like a Local tours to learn even more about the neighborhood’s history. They have quite a few options that’ll take you to major landmarks in the city as well as local eateries and drink spots.

Buy a few books at the Frugal Bookstore

When you’ve finished your tour, stop off at the Frugal Bookstore to pick up one (or ten) books to squeeze into your suitcase. Located in the historic Nubian Square, it focuses on amplifying BIPOC authors and has tons of popular options brand new.

Where to Eat During Your Weekend in Boston

There are so many incredible places to eat in Boston, it’s going to be harder for you to narrow them down! However, here are a few options to get you started.

Little Italy, North End

If there’s one place you go to for food, make it Boston’s North End, better known as Little Italy. Italian-Americans make up the second largest single ethnic group in the city after the Irish, and many settled in North End after immigrating through the Port of Boston. As they created their community in this .36 square miles of land, they brought with them all the best of their culinary traditions so that today you can find all sorts of authentic trattorias, pizzerias, bakeries, and more.

You really can’t go wrong with any of the places you choose, but some standouts include:

• Bricco Salumeria & Pasta Shop – founded by the “mayor” of Little Italy, Frank DePasquale, to offer up the kind of goods he grew up with near the Amalfi Coast. Stop in for lunch for one of their sandwiches; I’m partial to the Italian option.
• Mare Oyster Bar – another of DePasquale’s restaurants and great for Italian-style seafood.
• Modern Pastry – perfect dessert place for Italian pastries, especially cannolis.
• Regina Pizzeria – opened since 1926 and one of the best places in the city for pizza.

As a bonus, a number of historic landmarks are in North End, including many on the Freedom Trail, so you can do a little sightseeing before or after your meal.

Union Oyster House

If there’s one place that’s carved out a place in both Boston’s cultural and culinary history, it has to be Union Oyster House. Even before it became a restaurant in 1826, the building was used for a variety of reasons as the country was fighting for independence.

Back during the lead up to the war, it saw Isaiah Thomas print copies of The Massachusetts Spy, a crucial political paper that helped plant the seeds for revolution. During the revolution a number of famous wives set themselves up here to help mend clothes. Also because Ebenezer Hancock, the first paymaster for the Continental Army, made the building his headquarters, George Washington himself was often visiting.

Even after it became a restaurant, it would go on to feed the who’s who of American political celebrities and Hollywood stars over the next two centuries. There’s even a Kennedy Booth where you can sit where J.F.K. once ate every Sunday for lunch.

And don’t worry about the quality of the food. You don’t become America’s oldest continuously operating restaurant just because a bunch of famous people have eaten here. In 2020 alone, they won the North American Best Landmark Restaurant by the Wold Culinary Awards, and I can personally attest to their expertise shucking oysters and offering up the best in New England seafood!

Sichuan Garden  & Blossom Bar

If you want some truly delicious Chinese food, you’ve got to make reservations at Sichuan Garden. As the name suggest, the Duan family focuses on authentic dishes from Sichuan, China, which is where they’re from. While they have two locations, I’ve personally been to the beautifully decorated Brookline location.

This location also has Blossom Bar where son, Ran Duan, serves up award-winning, Latin-American influenced cocktails.

And there you have it, a number of ways to spend a historic weekend in Boston, Massachusetts! From food to history to getting outside, there’s so much to do, I bet this won’t be your last getaway.

If you want to see more on Boston and what else we got up on our visit, check out our Boston episode of Season 5’s “Samantha Brown’s Places to Love”!