A Weekend in Boston: Discover the Historic City

The birthplace of the American Revolution, Boston is one of the most historic cities in the United States. It’s home to the country’s oldest public park, university, public library and many other firsts that have given it a unique place in the nation’s cultural and political identity.

Modern Boston overflows with creativity and innovation across various fields, including literature, music, cuisine, technology, medicine, and architecture. Having grown up in the nearby suburbs, I find that every visit to the city reveals new experiences, diverse cultural influences, and evolving neighborhoods to explore, all while maintaining a distinctly Bostonian charm.

Thursday

Evening: If you arrive early enough to explore after checking into your accommodation, consider visiting the Trillium Beer Garden on the Rose Kennedy Greenway. This venue is perfect for a relaxed first evening in Boston during the warmer months. Conversely, Trillium’s year-round taprooms at Fort Point and Fenway are excellent alternatives in colder weather.

Friday

Morning: Start your day at the Boston Public Market on Hanover Street, where you can indulge in freshly baked cider donuts, savory crêpes, or sourdough bagels, alongside other products from local artisans.

How to spend the day: Immerse yourself in Boston’s revolutionary past by exploring the 2.5-mile Freedom Trail, which winds past key historic sites, beginning at the Boston Common, the oldest public park in America. Trace the red line in the pavement through downtown Boston, with stops at significant locations such as the Old State House, Faneuil Hall, and the Old North Church.

In the North End, treat yourself to a cannoli at Mike’s Pastry, a cherished Boston institution located just a block from the Paul Revere House. Nearby, Monica’s Mercato serves up some of the finest sub sandwiches in the city.

The Freedom Trail continues across the Charles River to Charlestown, home to attractions such as the Bunker Hill Monument and Museum, as well as the USS Constitution, the world’s oldest commissioned warship still in operation.

Dinner: After a day of sightseeing, you’ll likely want to refuel at one of Boston’s excellent restaurants. Head to the Seaport, a revitalized industrial area now boasting remarkable dining options, including Legal Sea Foods, an iconic Boston eatery with indoor and seasonal outdoor dining. Nearby, The Barking Crab offers fresh seafood in a casual setting overlooking the Fort Point Channel.

After dark: Boston’s vibrant cultural scene spans concerts, theater, and performing arts. If you haven’t prearranged plans, the Bostix booth at Faneuil Hall Marketplace is excellent for last-minute deals on available shows.

Saturday

Morning: Now that you’ve delved into Boston’s early history, venture to the Back Bay, an area developed in the 19th century on reclaimed land. Start with a refreshing walk along the Charles River Esplanade, then savor coffee and pastries at Tatté Bakery. Alternatively, enjoy a late breakfast at Beacon Hill Books & Café on Charles Street (reservations recommended).

How to spend the day: The Back Bay features some of Boston’s finest art museums, including the stunning Isabella Stewart Gardner Museum and the impressive Museum of Fine Arts (MFA). The Gardner Museum requires timed admission; therefore, reserving tickets in advance is advisable to ensure entry.

If art isn’t your preference, consider visiting Fenway Park, the oldest Major League baseball stadium, where you should buy tickets well in advance for a game. Guided tours are available year-round when there’s no game occurring.

After exploring your selected iconic Boston venue, return towards downtown, walking past the striking brownstones lining the leafy Commonwealth Avenue and Newbury Street, one of Boston’s renowned shopping destinations.

Stop for ice cream at JP Licks, or consider Sonsie for a meal. A short detour to Copley Square reveals historic sites such as Trinity Church and the Boston Public Library, an architectural gem worth exploring. Take some time to relax in the beautiful Boston Public Garden ahead of the evening festivities.

Dinner: For a unique dining experience, consider a reservation at Yvonne’s, a charming downtown supper club known for its exquisite drinks and shareable dishes. Alternatively, head to the South End for a variety of dining choices, including delicious Asian cuisine at Myers + Chang and tapas at Toro.

After dark: Having seen Boston from the street level, consider admiring the city from above. Head to View Boston at the Prudential Center, the city’s second tallest building, for stunning 360-degree views. Choose between the floor-to-ceiling windows of the indoor viewing area on the 52nd floor or the open-air rooftop terrace and bar one level below to enjoy the twinkling lights of the city and potentially a striking sunset.

Sunday

Morning: While in Boston, make sure to cross the Charles River to Cambridge, another vibrant city known for being home to two of the world’s premier universities, Harvard and the Massachusetts Institute of Technology (MIT).

Start with a scenic walk across Memorial Drive from the Longfellow Bridge to Massachusetts Avenue, enjoying views of the Back Bay skyline. For a morning boost, visit Flour Bakery, a beloved local chain with various locations in Boston and Cambridge.

How to spend the day: Harvard, founded in 1636, is the oldest and arguably the most prestigious university in the United States. Known from numerous films and television shows, the Harvard Yard boasts lush quadrangles surrounded by iconic red-brick buildings, including the renowned Widener Library. Nearby, you’ll find several fantastic museums associated with the university, like the Harvard Art Museums and the Harvard Museum of Natural History.

The commercial district around Harvard Square may have undergone gentrification, but it still offers excellent dining options or sweet treats at LA Burdick, renowned for its delicious handcrafted chocolate and rich drinking chocolate. Book lovers should visit the Harvard Book Store, one of the most celebrated bookstores in the Boston area.

While there is much to see and do, it may soon be time to hop back on the T and head towards Logan Airport. Many travelers leave with dreams of their next visit to this captivating city, which continually evolves while remaining quintessentially Boston.

This article was first published Jul 3, 2019 and updated Oct 11, 2024.