Summary
Downtown Boston represents one of the oldest settlements in North America, with a lineage tracing back to the arrival of the Puritans in the early 1600s. Over the centuries, Boston has been integral to pivotal historical events, including the American Revolution, which are commemorated throughout the downtown area.
Discover the Downtown district where you can explore seventeenth-century architecture amidst modern skyscrapers, enjoy oysters in a historic restaurant that has been operating since the early 1800s, or experience moments that shaped America’s history through reenactments aboard a floating tall ship museum.
Moreover, Downtown Boston offers a wide array of attractions beyond historical sites, making it suitable for a diverse group of visitors. Here are fifteen of the top activities to ensure an engaging stay without overwhelming yourself with the past.
1. Codzilla Boat Cruise
Downtown Boston has deep maritime connections; however, the Codzilla Boat Cruise offers an exhilarating experience.
Board the seventy-foot-long speedboat at Long Wharf and prepare for a thrilling ride as it accelerates to speeds of up to forty miles per hour while skillfully navigating the waters with impressive spins. The adventure can be wet, so plan on having a change of clothing.
If the thrill of Codzilla exceeds your comfort, proceed to discover calmer and drier Boston harbor cruises available later.
2. Freedom Trail
Uncover Downtown Boston’s history by traversing the Freedom Trail. Begin your journey in comfortable footwear at either the Old South Meeting House on Milk Street or the Old Corner Bookstore on Washington Street.
Clearly marked by a dual line of red bricks, the two-and-a-half-mile trail winds through the district and beyond, leading you past sixteen of Boston’s most significant historical landmarks.
For an engaging and educational experience, consider taking a guided tour led by a costumed presenter at the ArtsBoston booth in Faneuil Hall Marketplace, where you’ll witness the historical tapestry of Downtown Boston come to life.
3. Downtown Crossing
Explore Downtown Crossing for a pedestrian-friendly shopping experience, situated at the intersection of Winter, Summer, and Washington Streets.
This vibrant shopping hub features an abundance of jewelry stores and a variety of other retail shops, including food vendors and major department stores such as Macy’s, as well as theaters and numerous cafés and dining options.
4. Dreamland Wax Museum
Capture a memorable photograph alongside some remarkably lifelike wax figures at the Dreamland Wax Museum, located in Downtown Boston’s Washington Mall. The museum features twelve uniquely themed galleries spread over an expansive nineteen-thousand square feet of exhibition space.
Here, you can encounter renowned personalities including Snoop Dogg, Cher, Clint Eastwood, the Queen of England, and all forty-four Presidents of the United States.
5. Union Oyster House
It is uncommon for a restaurant to receive the distinction of being a historical landmark, yet the Union Oyster House on Union Street in Downtown Boston has achieved this honor. Operating for over two hundred years, it has remained celebrated for its oysters.
With its exterior resembling a medieval street, the Union Oyster House exudes historic charm. Inside, the atmosphere is characterized by bare wooden flooring and exposed beams, reinforcing its historical ambiance, along with a diverse menu rich in seafood.
Here, patrons can observe the shucking of oysters at the bar or indulge in dishes such as oysters Rockefeller and the extensive Ye Olde Seafood Platter. The quality of the ocean fare will undoubtedly satisfy your palate.
6. Boston Tea Party Ships and Museum
Experience the 18th-century replica tall ship moored off Congress Street in Downtown Boston that immerses you in a vivacious reenactment of a defining moment in North American history.
The Boston Tea Party Ships and Museum hosts costumed guides who portray key figures from this historical event. Participate in their meeting sessions, followed by an engaging session on the ship where tea chests are tossed overboard. Visitors can also tour the crew’s quarters and the ship’s hold.
Do not overlook the original tea chest from the 1773 Tea Party nestled within the museum, as well as enjoying tea and scones at Abigail’s Tea Room served by staff in period attire.
7. Trolley of the Doomed
For an unconventional sightseeing experience, consider going on a ghost-hunting tour in Downtown Boston. Board the Old Town Trolley at its Atlantic Avenue stop and prepare for a night filled with eerie tales.
Guided by a 17th-century grave digger, the tour narrates spine-chilling stories such as those of the Boston Strangler while exploring ancient burial grounds, Boston’s haunted hotel, and other reputedly haunted sites.
The Old Town Trolleys also provide a daytime hop-on-hop-off service that is free from ghostly tales throughout Downtown Boston.
8. Mr. Dooley’s Boston
Boston has showcased a rich Irish legacy since the mid-1800s, and amongst the many Irish-themed establishments, Mr. Dooley’s Boston on Broad Street stands out for its authenticity and quality.
For nearly three decades, Mr. Dooley’s has been a go-to for enjoying Guinness alongside traditional Irish breakfast. Evening hours bring an atmosphere of authentic Irish festivities with regular live music and occasional spontaneous fiddle performances.
9. Rose Kennedy Greenway
Visit the Downtown Boston waterfront to take a leisurely stroll through the Rose Kennedy Greenway, a beautiful expanse of seventeen acres that stretches over a mile through the district and into neighboring areas.
The Greenway consists of seven individual parks interconnected by wide promenades, interactive fountains, thoughtfully landscaped gardens, and a variety of public artworks, including a charming carousel featuring native Massachusetts animals.
This park is an ideal place for fresh air, and it offers beautiful vistas of the Downtown skyline. Should your walk incite hunger, an array of over thirty food trucks await along the Greenway for a delightful snack.
10. The Wilbur
For an exceptional evening filled with comedic performances or captivating music, the Wilbur Theater on Tremont Street stands out as the premier venue in Downtown Boston.
First opened in 1914 and capable of accommodating eleven hundred attendees, this historic theater is a treasured landmark in Boston. While its exterior appears unassuming, the interior reveals an ornate Renaissance-style decor, offering mezzanine, balcony, and orchestra seating with full bar service available.
11. Sunset Cruise
Embark on a journey from Long Wharf in Downtown Boston during dusk aboard a Boston Harbor Cruise Boat to witness the stunning Downtown skyline against the backdrop of a magnificent Massachusetts sunset.
Guests can select between a ninety-minute narrated cruise that coincides with the evening cannon firing on the USS Constitution or a one-and-a-half-hour trip across the harbor, inclusive of music, light refreshments, and sunset cocktails.
Additionally, ninety-minute daytime excursions around the harbor, featuring professional narrations about Boston Harbor’s history, are also available.
12. Durgin-Park Restaurant
For an authentic dining experience steeped in history in Downtown Boston, visit the Durgin-Park Restaurant situated on North Market Street. Established in 1827, this vintage-style restaurant has been serving traditional Boston cuisine to its patrons since prior to the American Civil War.
Make your visit memorable by trying their famed Boston Baked Beans, Clam Chowder, or the comforting Baked Indian Pudding.
The Gaslight Pub on the street level serves the full menu along with a special happy hour food offering and an outdoor seating area.
13. Chinatown Gate
Stroll along Beach Street in Downtown Boston and be captivated by the sight of an elaborate pagoda-style structure adorned with Chinese characters ahead.
Passing through the Chinatown Gate, you will immerse yourself in a distinct culture. Boston’s Chinatown is the third-largest in North America, with roots tracing back to the 1840s.
This vibrant area is full of restaurants, shops, and hosts various street festivals throughout the year, including the August Moon Festival and the Chinese New Year celebrations.
14. Down Boston
For an exciting nightlife experience, consider Down Boston located on High Street in Downtown Boston as your venue of choice.
This stylish nightclub situated underground features a spacious dance floor surrounded by cozy booth seating, illuminated by a captivating array of LED lighting.
Renowned Boston DJs take command of the decks, spinning the latest dance music, ensuring a vibrant atmosphere until at least two in the morning.
15. Make Way For Ducklings
Although not precisely within Downtown Boston, the Make Way For Ducklings statues can be found a short walk away in Boston Common, adjacent to the Boston Gardens, and warrant a visit during your exploration of the district.
The sculptures pay homage to a beloved children’s story set in the city, achieving a level of iconic status comparable to some of the district’s historical sites.
The proud mother duck and her eight ducklings provide a charming and highly Instagrammable photo opportunity, making them a must-see.
