15 Best Things to Do in Downtown Boston

Downtown Boston is one of the oldest settlements in North America and has a history dating back to the arrival of the Puritans in the early 1600s. Throughout the centuries, Boston has played an important role in major historical moments including the American revolution and those notable events are celebrated throughout the downtown district.

Explore the Downtown district to discover seventeenth-century buildings between modern-day skyscrapers, eat oysters in a restaurant open since the early 1800s or live the moment which changed America’s history in a re-enactment aboard a floating tall ship museum.

Don’t think Downtown Boston is just for history fans; it’s not. There’s much more to see and do there than visit museums. Don’t miss out on any of these fifteen of the best things to do in Downtown Boston to make sure you have a great stay without getting an overload of the past.

1. Codzilla Boat Cruise

Downtown Boston has a strong attachment to maritime history, but forget all about that when it comes to the Codzilla Boat Cruise.

Board the seventy-foot-long speedboat at its moorings on Long Wharf and get ready for a full-on thrill ride. The boat hits speeds of up to forty miles per hour as it zooms across the water and spins through a full three-hundred and sixty degrees. Yes, it’s wet and wild, so take a change of clothes.

If Codzilla is too much, scroll down to read about more sedate, stay dry, Boston harbor cruises further on.

Book online: Boston Harbor Codzilla High Speed Thrill Boat

2. Freedom Trail

Boston’s Freedom Trail Walk

Explore Downtown Boston’s past by walking the Freedom Trail. Put on some comfortable shoes and join the trail in Downtown at the Old South Meeting House on Milk Street or by the Old Corner Bookstore on Washington Street.

The two and a half mile trail is clearly marked by a double line of red bricks in the pavement and runs through the district, as well as outside its boundaries, and past sixteen of Boston’s most notable historical landmarks.

For a fully immersive and informative experience, join a tour narrated by a costumed guide at the ArtsBoston booth in Faneuil Hall Marketplace. They do a fantastic job of bringing Downtown Boston’s history to life.

Recommended tour: Freedom Trail History and Architecture Walking Tour

3. Downtown Crossing

Downtown Crossing, Boston

Source: Keith J Finks / shutterstock

Downtown Crossing

Head to the Downtown Crossing for some traffic-free retail therapy. The Crossing, located at the junction of Winter, Summer and Washington Street, is a pedestrianized shopping zone and the best place in Downtown Boston to pick up a bargain.

Downtown Boston is well known for having more jewelers shops than restaurants, and there are plenty on the streets of the Crossing. There are also numerous other retail outlets ranging from street food vendors to large department stores like Macy’s, theaters and more than a handful of coffee shops and eateries.

Related tour: Downtown Harbor Sailing Cruise

4. Dreamland Wax Museum

Dreamland Wax Museum

Snap a souvenir photo with some of the wax effigies in the Dreamland Wax Museum in Downtown Boston’s Washington Mall. The wax figures of top stars and politicians are so realistic, convincing friends you met the real person won’t be a big deal.

The museum has twelve differently themed galleries covering a total floor space of over nineteen-thousand square feet. Get up close to Snoop Dogg, Cher, Clint Eastwood, the Queen of England and all forty-four presidents of the US.

Available online: Dreamland Wax Museum Entry Ticket

5. Union Oyster House

Union Oyster House

Source: Wangkun Jia / shutterstock

Union Oyster House

It’s not often a restaurant is designated as a historical landmark, but it’s one honor which has been bestowed on the Union Oyster House on Union Street in Downtown Boston which has been serving oysters to its customers for over two-hundred years.

With a facade more in keeping with a medieval street than a modern US city, the Union Oyster House looks every bit as historic as it is. The interior of bare wood flooring and beamed ceiling continues the time-warp impression, and there are still plenty of oysters on the menu.

Watch the oysters being shucked while sitting at the bar or take a table and fill up on oysters Rockefeller or go all out with a Ye Olde Seafood Platter. The taste and quality of the seafood won’t disappoint.

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6. Boston Tea Party Ships and Museum

Boston Tea Party Ships and Museum

Source: LnP images / shutterstock

Boston Tea Party Ships And Museum

Visit the 18th-century replica tall ship at its moorings just of Congress Street in Downtown Boston and be immersed in a live reenactment of a moment which changed the history of North America.

At the Boston Tea Party Ships and Museum, costumed guides portray the roles of the characters involved in the historic event. Join them at the meeting house as rebellion flares before heading onto the decks of the ship to throw tea chests overboard the head below decks to explore the crew’s quarters and the hold.

Don’t miss viewing the 1773 original Tea Party tea chest housed in the museum or taking tea and scones in Abigail’s Tea Room served by waitresses in colonial dress.

Highly recommended: Boston Tea Party: Ships & Museum Interactive Tour

7. Trolley of the Doomed

Old Town Trolley Tours

Source: travelview / shutterstock

Old Town Trolley Tours

Forget conventional sightseeing and go spook spotting in Downtown Boston instead. Get on the fright night special Old Town Trolley at the stop on Atlantic Avenue and be ready for some serious goosebumps raising.

The ghost tour is narrated by a 17th-century gravedigger who regales listeners with tales of the Boston Strangler while visiting ancient haunted burial grounds, Boston’s most haunted hotel and other locations in DT where spooks are reputed to wander.

The Old Town Trolleys also operate a daytime, spook-free, hop-on-hop-off service throughout Downtown Boston.

Book online: 1.5-Hour Ghosts and Gravestones Tour

8. Mr. Dooley’s Boston

Mr. Dooley's Boston

Source: m_sovinskii / shutterstock

Mr. Dooley’s Boston

There has been an Irish influence in Boston since the mid-1800s and there’s no shortage of Irish-themed bars, but for a good pint and a dash of authenticity, drop into Mr. Dooley’s Boston on Downtown Boston’s Broad Street.

Dooley’s have been serving Guinness alongside their Irish breakfast in the district for almost three decades. At night, be ready for some proper Irish shenanigans with regular live music and the occasional impromptu fiddle session.

9. Rose Kennedy Greenway

Rose Kennedy Greenway

Source: Radomir Rezny / shutterstock

Rose Kennedy Greenway

Head along to the Downtown Boston waterfront for a stroll through the Rose Kennedy Greenway. The Greenway is seventeen acres of parklands which stretch for over a mile through the district and into adjacent neighborhoods.

The Greenway is comprised of seven individual parks connected by broad promenades, plazas with interactive fountains, landscaped gardens and multiple public artworks plus a fun carousel with figures depicting animals native to Massachusetts.

Not only is the Greenway a great place to get a breath of fresh air, it’s also the perfect spot for seeing some great views of the Downtown skyline. If the exercise brings on an appetite, don’t worry, there are over thirty food trucks on the Greenway from where to purchase a snack.

10. The Wilbur

The Wilbur

Source: PhillipJR / shutterstock

The Wilbur

For an unforgettable night of comedy or music from top American and international stars, there’s nowhere better to go in Downtown Boston than the Wilbur Theater on Tremont Street.

The one-thousand-one-hundred seat theater first opened in 1914 and is one of the city of Boston’s historic landmarks. Externally plain, the theater is Renaissance-style ornate internally and has mezzanine, balcony, and orchestra levels each with full bar service.

11. Sunset Cruise

Boston Skyline At Sunset

Source: Vlad G / shutterstock

Boston Skyline At Sunset

Sail out from Long Wharf in Downtown Boston at dusk aboard a Boston Harbor Cruise Boat to view the sensational DT skyline and an impressive Massachusetts sunset.

Choose from a ninety-minute narrated sailing which coordinates with the end of the day cannon firing on the USS Constitution or a one and a half hour trip across the harbor waters with music, light snacks, and sundowners included.

Ninety-minute daytime cruises around the harbor are also available and include a professional narration on the history of Boston harbor.

Related tour: Boston Sunset Cruise

12. Durgin-Park Restaurant

Durgin-Park Restaurant

Source: PhillipJR / shutterstock

Durgin-Park Restaurant

For historic eats in Downtown Boston stop off at the Durgin-Park Restaurant on North Market Street. Established in 1827, this vintage-style eatery has been serving traditional Boston dishes to its clientele since before the American Civil War.

Don’t visit Downtown Boston without trying the Durgin-Park’s infamous Boston Baked Beans, Clam Chowder or heart-warming Baked Indian Pudding.

The street-level floor of the restaurant houses the Gaslight Pub which, as well as serving the full menu, has a special happy hour food offering and an outside patio.

13. Chinatown Gate

Chinatown Gate, Boston

Source: Zdenka Kincel / shutterstock

Chinatown Gate

Walk along Beach Street in Downtown Boston and be surprised by the sight of an elaborate, green-roofed pagoda-style structure with Chinese lettering straddling a street up ahead.

Pass through the Chinatown Gate and discover a completely different culture. The Chinatown in Boston is the third largest in North America and dates back to the 1840s.

Colorful and vibrant, Chinatown is full of restaurants, shops, and hosts many street celebrations throughout the year including the August Moon Festival and Chinese New Year.

Available tour: Chinatown Culture and Cuisine Walking Tour

14. Down Boston

Down Boston

For a mega-party night out, then Down Boston on Downtown Boston’s High Street is a great choice of venue.

The slick nightclub, located in a basement, has a good-sized dance floor surrounded by plush booth seating and positively glows with a neon rainbow of LED lighting.

Top Boston DJ’s man the decks spinning all the latest dance music, so be prepared to rave until at least two in the morning or later.

15. Make Way For Ducklings

Make Way For Ducklings, Boston

Source: Belikova Oksana / shutterstock

Make Way For Ducklings

While not strictly in Downtown Boston, the Make Way For Ducklings statues are just a stroll away over Boston Common in the adjacent Boston Gardens and a must-see when visiting the district.

The statues commemorate a children’s storybook about a duck family which was based in the city and have become almost as iconic as some of the district’s historical landmarks.

The proud mother mallard and her eight ducklings make for a great, and very Instagramable, souvenir photo of Downtown Boston. Don’t miss out on seeing them.

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Where to stay: Best Hotels in Boston, Massachusetts (MA)
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List of Image Sources

15 Best Things to Do in Downtown Boston:

Rose Kennedy Greenway

  • Codzilla Boat Cruise: Massachusetts Office of Travel & Tourism / Flickr
  • Boston’s Freedom Trail Walk: getyourguide.com
  • Downtown Crossing: Keith J Finks / shutterstock
  • Dreamland Wax Museum: Dreamland Wax Museum / Facebook
  • Union Oyster House: Wangkun Jia / shutterstock
  • Boston Tea Party Ships And Museum: LnP images / shutterstock
  • Old Town Trolley Tours: travelview / shutterstock
  • Mr. Dooley’s Boston: m_sovinskii / shutterstock
  • Rose Kennedy Greenway: Radomir Rezny / shutterstock
  • The Wilbur: PhillipJR / shutterstock
  • Boston Skyline At Sunset: Vlad G / shutterstock
  • Durgin-Park Restaurant: PhillipJR / shutterstock
  • Chinatown Gate: Zdenka Kincel / shutterstock
  • Down Boston: Down Boston / Facebook
  • Make Way For Ducklings: Belikova Oksana / shutterstock