What to Do in Southie (South Boston) in 2025

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Explore the best of South Boston with this guide. From waterfront walks to classic local spots, find out why Southie is worth a visit!

As a Boston local, I’ve spent plenty of time exploring Southie’s streets, and it never gets old! Right next to the Seaport and close to downtown, Southie blends classic charm with new spots popping up all the time. Whether you’re here for the waterfront, some local eats, or just want to explore, there’s always something going on.

This list pulls together my favorite things to do in South Boston, from popular hangouts to hidden gems. I’ve added practical tips based on my own visits to help you plan your activities. Here’s what to do in Southie. If you’re visiting or just curious about this side of Boston, I hope you find it useful!

1. Castle Island

Castle Island is my go-to spot when I need some fresh air. This New England gem is not actually an island anymore, but don’t let that stop you from exploring Fort Independence in the summer. The path around the water is perfect for a jog or a stroll, and you’ll often spot people fishing.

Sullivan’s, the snack bar, is practically a Southie institution. Their hot dogs and soft serve are my guilty pleasure after a walk. I recommend grabbing some food and finding a spot to watch planes landing at Logan.

Fair warning: it gets packed on sunny weekends, so come early if you want a parking spot. And don’t forget a jacket – it can be surprisingly windy out there, even on nice days. Trust me, I’ve made that mistake more times than I’d like to admit!

2. M Street Beach

On warm days, M Street Beach is one of the best places to visit in South Boston. It’s part of the beaches along Pleasure Bay and is perfect for a quick dip or just lounging by the water. The calm waves make it great for swimming, and it’s easily one of the best spots to relax in Southie.

If you’re up for a longer walk, follow the shoreline all the way to Carson Beach—you’ll get a great view of the entire coastline. Just be sure to pack sunscreen and water since there isn’t much shade.

Parking can be a hassle, so biking or taking the T is a solid bet. I love coming early in the morning for a quiet jog along the water before the crowds show up. It’s the perfect way to kick off a summer day in Southie!

3. The Institute of Contemporary Art (ICA)

Looking for a cool mix of art and amazing views? Head over to the Institute of Contemporary Art (ICA) on the South Boston Waterfront.

This place is a local gem in Boston with its edgy art exhibits and sleek, modern design. The building itself is like a piece of art, with floor-to-ceiling windows that offer killer views of the harbor. Trust me, the deck is the perfect spot to chill and take in the city vibes.

The ICA is always switching up its exhibits, so there’s something new to check out every time you go. From wild installations to thought-provoking pieces, it’s a great spot to get your culture fix without the usual museum stuffiness.

For one of the best free things to do in South Boston, visit the ICA on Thursdays after 5 pm when admission is free. It’s a great way to break up the week and explore something new without spending a dime. Just hop on the Silver Line to Courthouse Station, and you’re there!

4. Thomas Park

When I need a reminder of why I love this city, I head to Thomas Park. It sits on top of Dorchester Heights and has an incredible view of the skyline and harbor. There’s a monument from Revolutionary War times, which is cool if you’re into history.

It’s one of the best places to visit in Boston for a picnic on sunny days. The park isn’t huge, but there’s enough green space to throw a frisbee or relax on the grass. It’s particularly beautiful at sunset – the city lights starting to twinkle as the sky changes color is something special.

The walk up can be a bit of a huff and puff, but it’s worth it. Just bring a jacket – it can get breezy up there. There aren’t any facilities in the park itself, so plan accordingly. Parking is street-only and can be tight, but it’s usually not too bad.

5. South Boston Farmers Market

Every Monday from June to October, I recommend visiting the South Boston Farmers Market in the parking lot at 446 West Broadway. It’s not huge, but it’s got character. I always walk away with armfuls of fresh veggies and bread. The vendors change up from week to week, which keeps things interesting.

I love chatting with the local farmers. They always have some cooking tips I’d never think of! They often have live music too, which makes grocery shopping way more fun than it has any right to be. If you’re cooking your own meals, this is a great place to stock up on ingredients.

A heads-up: it can get busy right after work hours. Bring your own bags if you can. Oh, and they accept SNAP benefits, which is good to know. The market is weather-dependent, so check their social media if the weather looks iffy.

6. The Lawn on D

Wondering what to do in Southie in the summer? Head to The Lawn on D in the Seaport District. It’s a big outdoor space with lawn games and those Instagram-famous light-up swings. I’ve definitely taken my fair share of cheesy photos on them! They often have events or live music going on, which adds to the fun atmosphere, making it one of the best things to do in Boston.

It’s a great spot to meet up with friends after work. Grab a drink, play some lawn games, and maybe catch a sunset. The space is only open seasonally, usually from May through October. There’s no entry fee, which is nice.

It can get pretty packed on weekends, especially if there’s a special event going on. It’s family-friendly during the day, but has more of an adult vibe in the evenings. There’s some parking available, but taking the T to World Trade Center is often easier.

Check their website for the schedule of events – they do everything from art installations to fitness classes.

7. Amrheins

When I’m craving some old-school Southie vibes, I head to Amrheins. This place is a neighborhood institution – they say the bar is the oldest hand-carved bar in America. The food is classic American stuff, nothing fancy, but it hits the spot.

It can get busy, especially during dinner hours, so I recommend calling ahead for a table. The staff here are great, too. They’re always up for a chat about the neighborhood’s history. If you ask, they can tell you some interesting stories about the place.

Just remember they’re closed on Mondays. It’s a short walk from the Broadway T station. They have a small parking lot, but it fills up quickly. The portions are generous, so come hungry!

8. South Boston Candlepin

For a bit of old-school fun in Southie, you’ve got to check out South Boston Candlepin on E Broadway. This spot is a total throwback with its retro vibes and classic candlepin bowling – a New England favorite! It’s the kind of place where you can just kick back, roll some strikes (or gutter balls, no judgment!), and enjoy some good laughs with friends.

This local gem at 543 E Broadway is open Wednesday through Saturday. The no-frills atmosphere keeps things laid-back, and you can’t beat the prices. It’s great for a low-key date night, family outing, or just some spontaneous fun with your friends.

South Boston Candlepin is right along the 9 bus route, or a quick walk from the Broadway T station. And hey, don’t forget to grab a beer for the full experience!

9. Boston Harborwalk

For those who love a good stroll with a view, Boston Harborwalk is a must-do in Southie. This scenic path runs along the waterfront, offering unbeatable views of the Boston skyline, the harbor, and the boats cruising by.

What I love most the Harborwalk is that it connects you to some of South Boston’s best attractions. You can start near Castle Island and follow the path to the Seaport District, passing parks, piers, and plenty of places to grab a bite.

Remember to bring your camera. Believe me, you’ll want to capture the views, especially at sunset!

10. Harpoon Brewery & Beer Hall

If you’re looking for a laid-back spot to unwind in Southie, is a must-visit. Known for its local craft beers, Harpoon offers brewery tours that take you behind the scenes to see how the magic happens. The beer hall vibe is casual and fun, with long communal tables perfect for gathering with friends.

I highly recommend grabbing a flight to sample different brews. Don’t miss their famous pretzels, either! They’re freshly baked and served with a variety of dips. It’s an ideal spot to relax after exploring the neighborhood or to start your Boston night out.

It can get busy, especially on weekends, so consider booking a tour ahead of time. Street parking is limited, so taking the T to South Station and walking over is a good option.

Frequently asked questions (FAQs) about things to do in Berchtesgaden

Curious about the most picturesque tiny house designs? Our FAQs have all the answers!

Is South Boston worth visiting?

Yes, South Boston is definitely worth visiting. It’s got a great mix of beaches, local spots like Castle Island, and cool places to hang out like the Seaport District. Whether you’re into history, grabbing a bite, or just strolling by the harbor, there are always fun things to do in Southie—making it a true gem in Massachusetts.

What is Southie known for?

Southie is known for its strong Irish-American heritage, waterfront views, and places like M Street Beach and Castle Island. It’s also home to the lively St. Patrick’s Day Parade and has a mix of trendy spots and classic neighborhood vibes that make it uniquely Boston, making it a great place to stay in Massachusetts.

Is Southie a good neighborhood in Boston?

Yes, Southie is a good neighborhood in Boston. It’s got a mix of young professionals, families, and long-time residents, creating a tight-knit community. With lots of parks, bars, and restaurants, plus easy access to downtown, it’s a convenient and vibrant place to live in Boston.

Is South Boston walkable?

South Boston is very walkable. You can easily explore the beaches, parks, and local shops on foot, making it one of the top places to live and visit in Massachusetts. The main streets like Broadway are lined with everything from cafes to markets, which makes it easy to get around without a car.