20 Best Things To Do In South Boston, Massachusetts

things to do in south boston
| 9 min read

South Boston, Massachusetts, is located south and east of the Fort Point Channel. Home to about 40,000 people, it’s one of the best places to visit in Massachusetts. This neighborhood boasts several parks and a 3-mile (4.83 km) stretch of beach. If you are planning a vacation or a rest from the hurdles of life, you can choose this beautiful neighborhood. There are plenty of Airbnb vacation rentals in and around South Boston. You will have several Vrbo vacation rentals to choose from too. The city is home to several museums, restaurants that offer local drinks and food, and breweries. You can enjoy a walk around the city and soak in the beautiful city views. Your kids will have a great time at the second-largest Children’s museum perched in this town. Whether alone or as a group, scroll down to discover the best things to do in South Boston, Massachusetts.

1. Take a stroll around Columbus Park

Columbus Park, Boston MA
Source: Photo by Flickr user NNECAPA Photo Lib... used under CC BY 2.0

Columbus Park is located right by the harbor in the North End of South Boston. It is a beautiful park where you can enjoy a peaceful, enjoyable walk. The park is an accessible location in the city and it welcomes hundreds of visitors every week. Aside from the pleasurable walk around the park, you can enjoy lawn games. There is croquet to play here as well. If you feel like participating, there are people around to teach you how to play. There are also other games like corn hole and giant Jenga. You can also enjoy movies in this venue.

Columbus Park

Address: Boston, MA 02110, USA

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2. Take a leisurely walk at Thomas Park

Dorchester Heights National Historic Site South Boston MA 01
Source: Photo by Wikimedia Commons user Jameslwoodward used under CC BY-SA 3.0

One of the famous landmarks in South Boston, Thomas Park provides a glimpse into the rich history of the neighborhood. It is named in honor of Civil War General George H. Thomas and was once the site of the Dorchester Heights fortifications during the Revolutionary War, a crucial location in the fight for American independence. Today, Thomas Park is a picturesque destination that beckons visitors to take leisurely strolls along its winding pathways.

With its elevated position, it provides sweeping views of the Boston skyline and Boston Harbor, making it an ideal spot for a scenic walk. This serene urban oasis not only offers breathtaking vistas but also invites you to connect with the neighborhood’s historical roots while enjoying some peace and tranquility in the heart of South Boston.

Thomas Park

Address: Boston, MA 02127, USA

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3. Attend an exhibition at Boston Convention and Exhibition Center

The Boston Convention and Exhibition Center offers visitors a once in a lifetime experience. It is where you can enjoy an impressive technological experience. This center hosts some of the most technologically-advanced conventions on the planet. While here, you are bound to see and hear things that you have merely imagined. The exterior of the center boasts a beautiful yet intimidating architecture that you will find thrilling. There is free Wi-Fi; with network bandwidths bigger than any convention center you can think of.

Boston Convention and Exhibition Center

Address: 415 Summer St, Boston, MA 02210, USA

Website: Boston Convention and Exhibition Center

Opening hours: 7am - 10pm (daily)

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4. Go skating at Murphy Memorial Skating Rink

Ice skating in Porto
Source: Photo by Wikimedia Commons user Joseolgon used under CC BY-SA 4.0

Boston offers plenty of outdoor ice rinks every winter. If you happen to be in South Boston during this time, you can enjoy a fun, family-friendly, and cheap experience at Murphy Memorial Skating Rink. Managed by the Department of Conservation and Recreation, it is a safe place to come and enjoy ice skating. It is open to the public from Monday through to Sunday. The ice surface is excellent, and there is seating for folks below the boards. Come here with the kids and enjoy some great family time!

Murphy Memorial Skating Rink

Address: 1880 William J Day Blvd, Boston, MA 02127, USA

Website: Murphy Memorial Skating Rink

Opening hours: 9am - 11pm (daily)

Price: 60 USD

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5. Enjoy cocktails at GrandTen Distilling

GrandTen is an urban distillery where you can enjoy chilled drinks and cocktails. You can take a tour of the distillery and enjoy drink tastings. The guide is a bartender who will teach you the rich history of the building and the drinks on the menu. Afterward, you can have the bartender make you excellent beverages, and you might even end up taking a few bottles of rum home. The ambiance is unique, and everyone is friendly and welcoming.

GrandTen Distilling

Address: 383 Dorchester Ave, Boston, MA 02127, USA

Website: GrandTen Distilling

Opening hours: Sat: 1pm - 11:59pm; Sun: 1pm - 8pm; Thu: 4pm - 10pm; Fri: 4pm - 11:59pm (closed from Mon - Wed)

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6. Take a stroll in Castle Island

Castle Island lies at the end of Pleasure Bay Beach and it offers a beautiful view of the sea and Dorchester Bay. Relish not only the sights but also exciting picnics. You can stroll along the Harborwalk. If you have children in the group or the family, they will also have an enjoyable time here. There is a playground situated just on the beach. The playland is fenced to provide security, and you can fly a kite along the slopes in the area as well.

Castle Island

Address: 2010 William J Day Blvd, Boston, MA 02127, USA

Website: Castle Island

Opening hours: 6:30am - 7pm (daily)

Price: Free

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7. Take your dog to South Boston Bark Park

For folks that travel with their canine companions, it can be frustrating leashing your dog wherever you go. South Boston Bark Park is an off-leash dog park. The park is right next to Harborwalk and it is just a distance away from Street Beach. Your dog will certainly enjoy the freedom and fun that this site provides. Come with your Frisbee and enjoy a lovely morning with your dog. The venue has a gravel run, and it also has separate areas for different sizes of dogs. If the sun comes up while you’re still there, do not worry, there are plenty of trees that provide adequate shade.

South Boston Bark Park

Address: 1280 Columbia Rd, Boston, MA 02127, USA

Website: South Boston Bark Park

Opening hours: 6am - 8pm (daily)

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8. Take a walk around Fort Point

Fort Point Channel Historic District South Boston MA 04
Source: Photo by Wikimedia Commons user Jameslwoodward used under CC BY-SA 3.0

Fort Point is one of the fastest-growing neighborhoods and one of the best tourist attractions in Boston’s south end. The neighborhood borders Seaport and downtown South Boston and it is a haven of many points of interest for the visitor. Walk along the streets of this neighborhood and enjoy the stunning view of city life. It lies by the water and is home to several museums, restaurants, and pubs. You can branch at Trillium Brewing Company and have a chilled bottle of beer. Whenever you come to South Boston, do not forget to visit this beautiful and thrilling part of it.

Fort Point

Address: New England, Boston, MA, USA

Website: Fort Point

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9. Play soccer at Joe Moakley Park

Posted by Massflag league on Tuesday, 16 April 2019

Joe Moakley Park is named after John Joseph Moakley, a famous politician born in South Boston. The park is an excellent location to come with your family or group of friends. There is a parking lot close to the track for your convenience. It is also a short distance from the JFK train station in South Boston. It is an urban park that features a different area - including a baseball field, a track field, and a stadium where you can play some soccer. It is located right across Dorchester beach and offers a beautiful view of the area. Come here for a run early in the morning, or with your kids for fun-filled moments at the waterpark.

Joe Moakley Park

Address: 1005 Columbia Rd, Boston, MA 02127, USA

Website: Joe Moakley Park

Opening hours: 24 hours (daily)

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10. Explore Andrew Square

Editor's Note: There's no photo available at the time of writing

Andrew Square is a vibrant neighborhood named after John Albion Andrew, a former Massachusetts governor and a staunch abolitionist during the Civil War era. Over the years, Andrew Square has undergone revitalization, becoming a hub for dining, entertainment, and community life. Visitors can savor a variety of culinary delights in the numerous restaurants and bars that have sprung up in recent years.

Its central location makes it an ideal starting point to explore the best of South Boston. The neighborhood’s proximity to public transportation also makes it easy to access other parts of Boston.

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11. Enjoy the view from Dorchester Heights

Dorchester Heights National Historic Site South Boston MA 02
Source: Photo by Wikimedia Commons user Jameslwoodward used under CC BY-SA 3.0

Dorchester Heights is located in the central area of South Boston. It is a hilltop, and it offers an unrivaled view of the surrounding area. Take a climb up this historic hill with friends and get a panoramic view of the regions to the south and west of South Boston. Plan your ascent up this hill on the 4th of July. You will enjoy some of the most beautiful fireworks displays ever as the surrounding communities launch their fireworks throughout the evening.

Dorchester Heights

Address: Thomas Park off Telegraph St., near G St., Boston, MA

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12. Enjoy a delicious barbecue at Stats Bar & Grille

Editor's Note: Photo taken from the establishment's official social account

At some point during your visit to this bustling location, you might find yourself craving some delicious barbecue. If so, there are plenty of spots to get your fix. However, none of them can satisfy you as well as Stats Bar & Grille. Located in the heart of South Boston, this spot offers excellent food and a wonderful time. Catch up with friends while seated comfortably in this warm restaurant. Enjoy the bacon cheeseburger, chicken club sandwich, or any of the delicious food offered. It is a lovely spot to hang out with your friends or family.

Stats Bar & Grille

Address: 77 Dorchester St, Boston, MA 02127, USA

Website: Stats Bar & Grille

Opening hours: Sat - Sun: 10am - 1am; Mon - Fri: 11am - 1am

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13. Sunbathe on M Street Beach

Posted by Barbie Welch on Tuesday, 10 September 2019

M Street Beach is one of the best beaches on this side of the state. It is part of a 3-mile (4.83-km) stretch of beach in South Boston. If you want to have a local feel of the beaches in this town, head over to this beach. The sand is soft and feels great between your toes. Relax from the stress of the city while here. The beach features public bathrooms and provides free parking. The kids will love playing here because aside from the attraction of the sand and water, there is also an ice-cream truck. Come and sunbathe or take a relaxing stroll.

M Street Beach

Address: William J Day Blvd Hull, Massachusetts 02127

Website: M Street Beach

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14. Visit the Vietnam War Memorial

Vietnam War Memorial South Boston Massachusetts

Posted by John Caputo on Saturday, 26 September 2015

War memorials are built to remember the brave souls that fell while in defense of a country. Boston is one of the oldest cities in America; hence, it is not surprising that it is home to several war memorials. The Vietnam War Memorial in South Boston is one of the most prominent. Take some time out of your trip to South Boston to visit this spot. This memorial has the names of the locals who fought in the Vietnam War and lost their lives in the conflict. Aside from the Vietnam war, it also remembers those who fell in the conflicts of Cambodia and Laos.

Vietnam War Memorial

Address: 172 Morrissey Blvd, Boston, MA 02125, USA

Website: Vietnam War Memorial

Opening hours: 24 hours (daily)

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15. Enjoy live music at Rockland Trust Bank Pavilion

Posted by Rockland Trust Bank Pavilion on Saturday, 27 July 2019

An outdoor amphitheater in South Boston, Rockland Trust Bank Pavilion is one of the most popular and fun places in the city. The amphitheater often serves as the location for several shows. The Pavilion has a seating capacity of up to 5,000 people and it is one of the best places to enjoy live music in the city. Experience listening to music via a state-of-the-art sound system, and feel the cool harbor breeze blowing against your cheek. Located just 4.1 miles (6.6 km) from Logan Airport, it is perched on a prime spot. You can also enjoy wine, champagne, or beer on the grounds.

Rockland Trust Bank Pavilion

Address: 290 Northern Ave, Boston, MA 02210, USA

Website: Rockland Trust Bank Pavilion

Price: 41 USD

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16. Have a beer at Harpoon Brewery and Beer Hall

If you are traveling in a group, Harpoon Brewery and Beer Hall is an excellent spot for the group to enjoy a drink. Located in the district of Seaport in Boston’s south end, this brewery offers visitors a whole day of fun. Although the trip to the brewery lasts for only an hour, the experience will be with you long after you leave. There’s a beer hall located in Harpoon Brewery and it is a great experience. Benches are lined up old-school style, and you can order exclusive beers in the Hall. The tour takes you around the Brewery, showing the process of making beer and the history of the Brewery. At the end of the trip, you end up back in the Beer Hall for more beer!

Harpoon Brewery and Beer Hall

Address: 306 Northern Ave, Boston, MA 02210, USA

Website: Harpoon Brewery and Beer Hall

Opening hours: Fri - Sat: 11am - 11pm; Sun - Thu: 11am - 8pm

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17. Let the kids have fun at Boston's Children Museum

Boston Children's Museum
Source: Photo by Wikimedia Commons user Tim Pierce used under CC BY-SA 3.0

If you will be visiting with children, Boston’s Children Museum is an exciting place to go. It is located just by the Boston Convention and Exhibition Center and offers a beautiful experience for the kids. The museum was established in 1913 and is the second oldest children’s museum in the country. The kids will enjoy the exhibitions that focus on science, art, culture, and the environment. The museum boasts a collection of more than 50,000 items, which is one of the largest collections in a Children’s museum.

Boston's Children Museum

Address: 308 Congress St, Boston, MA 02210, USA

Website: Boston’s Children Museum

Opening hours: Fri: 10am - 9pm; Sat - Thu: 10am - 5pm

Price: 17 USD

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18. Enjoy an amazing view at Fan Pier Park

Long exposure sunset photo taken at fan pier park in south Boston! #dslr #photography #boston

Posted by Brennan Kauffman photography on Saturday, 21 September 2019

One of the things South Boston is known for is its waterfront. Te Fan Pier Park is one of the several parks located along that waterfront. Enjoy a preview of the daily activities of the residents. The park offers a fantastic view of the surrounding area, and it is a beautiful spot to relax. The park also has plenty of chairs and tables so you can even enjoy a waterside picnic! There is also a lookout terrace for your benefit.

Fan Pier Park

Address: 1 Marina Park Drive, Boston, MA 02210, USA

Website: Fan Pier Park

Price: 17 - 38 USD

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19. Dine at Lincoln Tavern & Restaurant

Editor's Note: There's no photo available at the time of writing

Lincoln Tavern & Restaurant is a restaurant right in the heart of this beautiful city. It welcomes guests with exceptional, homemade, delicious food. No matter where you are from, you will enjoy dining at Lincoln Tavern & Restaurant. The restaurant serves diners a mixture of homemade, all-American meals, both classic and contemporary. The menu contains all you need to have an enjoyable dining experience. You can enjoy custom meals, cakes, and so much more. Come here alone or with your friends to enjoy a taste of Boston’s best delicacies.

Lincoln Tavern & Restaurant

Address: 425 W Broadway, South Boston, MA 02127, USA

Website: Lincoln Tavern & Restaurant

Opening hours: Sat - Sun: 9am - 2am; Mon - Fri: 10am - 2am

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20. Enjoy a picnic in South Boston Maritime Park

South Boston Maritime Park is an award-winning park that is located in the busy Seaport District. It features a beautiful and large lawn, a state-of-the-art three-season café which boasts outdoor seating, and other impressive features. It is a gorgeous park. Visit for a romantic stroll or picnic with your lover. As a maritime park, evidence of its heritage is seen all around it. The park also features pergola structures, magnificent trees that provide adequate shade and excellent lighting.

South Boston Maritime Park

Address: Boston, MA 02210, USA

Website: South Boston Maritime Park

Opening hours: 6am - 11:30pm (daily)

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Have fun in South Boston, Massachusetts

Dorchester Heights Historic District South Boston MA 01
Source: Photo by Wikimedia Commons user Jameslwoodward used under CC BY-SA 3.0

Loads of fun activities in South Boston, Massachusetts, await you to indulge in. Whether you are here to unwind or work, you can rest assured that you will leave this city feeling exhilarated and refreshed. As you plan your next vacation, why don’t you add South Boston to the list of places to go? You will immensely enjoy your visit with these top things to do in South Boston, Massachusetts.

For your accommodations, consider staying in one of the top Vrbo vacation rentals in and around South Boston. There are several Airbnb vacation rentals to choose from as well.

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Frequently asked questions about things to do in South Boston

  • Which are some of the fun activities for couples in South Boston?

    If you would like to engage in fun activities and spend quality time with your partner during a holiday in South Boston, you can go skating at Murphy Memorial Skating Rink, enjoy cocktails at GrandTen Distilling, take a walk around Fort Point, or explore Andrew Square together.

  • Which restaurants in South Boston can one visit for a delicious menu?

    If you are a connoisseur of good food and wine and would like to explore some of the best restaurants in South Boston during a trip here, you can enjoy a delicious barbecue at Stats Bar & Grille, have a beer at Harpoon Brewery and Beer Hall, or dine at Lincoln Tavern & Restaurant.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Ibrahim is a passionate writer with a keen interest in traveling. He not only travels to discover the world but also himself. And when it comes to writing, Ibrahim loves to keep it simple with a...Read more

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