Things to do at night in Boston to experience the city like a local

There are so many fun things to do in the Boston area that don’t involve Fenway Park or the Freedom Trail, especially if you're heading out for a night in Beantown. With classic Irish pubs and mainstays like the bar from Cheers alongside an underrated dining scene in East Boston, it's easy to put together an evening itinerary, worth the flight out to the capital of New England.  

Boston is not necessarily a place you want to visit during the winter, but there are enough drawers like live music and world-class dining that make it an appealing place to visit any time of year. The Prudential Center, in Back Bay, is the perfect place to do some evening shopping and grab a bite out of the elements. During the summer and fall? This city could not be better as you’ll enjoy comfortable temperatures even after the sun goes down. 

There's also an efficient public transportation network connecting Cambridge, downtown Boston, Somerville, and half a dozen other vibrant neighborhoods. And if you need to get around but still have your bags, Bounce has dozens of convenient Boston luggage storage locations and useful features to help take the stress out of your night out.

What to do in Boston at night if you’re looking for…

 An evening outdoors

When the weather is right, there's nothing better than hanging out under the night sky at one of Boston's rooftop bars or patios. 

Hit the Esplanade

The Charles River Esplanade snakes through Central Boston, providing a lovely bit of greenery. While its leafy paths are perfect for walking or cycling during the day, its patios overlooking the waterfront are what make it the perfect destination for an evening outdoors. If you're planning on enjoying an evening on the Esplanade, drop your bags off at a nearby Bounce location, so you can stroll more freely. 

Pro tip: Hit up Night Shift Brewing, which set up an open-air tap room to serve Bostonians its hoppy IPAs and refreshing lagers for summertime sipping under the stars.

Take a stroll along Boston Harbor

There's no better view of the Boston skyline than from its historic harborfront, especially at night when the city lights illuminate the bay. Boston Harbor is safe and enjoyable any time of day, but you can head to Fan Pier Park for the best of views and plenty of people watching. 

Rooftop dining and drinking

When the summer finally arrives in Boston, the nightlife scene does a complete 180 and heads outdoors. Just about every neighborhood has a rooftop terrace restaurant or bar. The Lexington in Cambridge has a rooftop patio and greenhouse where you can enjoy stylish cocktails and elevated bar bites. Trillium Brewing Company, Mare Oyster Bar, and Contessa (North End quality Italian food) are other favorites with popular patios where you want to get there a little early to snag a table. 

Pro tip: Keep an eye out for special events throughout the summer, like the Cambridge Dance Party in June

See the Boston skyline from the water

Treating yourself to a sunset cruise is a go-to for most tourists heading to Boston during the summer. And while some locals may dismiss it as a tourist endeavor, there’s simply no better view of the city skyline in downtown Boston than from a boat on the harbor. And when said boat serves you cocktails? It could be worse! Just remember that a boat is no place for your roller bag, you can stop by a Bounce facility to drop off the luggage. 

A decadent foodie evening 

While New York’s culinary scene gets all the headlines, Boston quietly offers one of the most intriguing destinations in the country. You might speculate that it's a lot of corned beef and cabbage, but Boston's restaurants are much more diverse than your expectations. 

Eat all the pasta in the North End

Boston’s Little Italy, North End, is a can’t-miss dining destination for anyone who loves wine, pasta, and Negroni's (what's not to love?)

Pro tip: Mike’s Pastry and Bova’s Bakery are two mainstays during the day, but you'll want to look into a table at an intimate trattoria to sample the best of Boston’s Italian cuisine. 

Grab some street food at Quincy Market in Faneuil Hall Marketplace

From classic lobster rolls to ramen, you'll have the full breadth of Boston's impressive variety on offer at this trendy complex near the Boston cruise terminal. Oh, and there’s beer! If you're just getting into Boston from a cruise, you can store your luggage at a nearby Bounce location before heading to Quincy Market. 

The South End ain’t bad either

The South End is situated in the heart of Boston and features some of the greatest hits of the city's dining scene. You’ll be able to hit mainstays like Delux Cafe and Greystone Cafe on your way to iconic landmarks like the Freedom Trail or Boston Common.

Pro tip: Exploring during the day? Charlie's Sandwich Shoppe is almost a century old and still one of the best diners in the city! 

An intellectual night out

If you weren’t aware, the home of MIT, Tufts, Boston College, and Harvard skews a little geeky. This highly parochial city takes pride in its illustrious academic heritage, and you would too if you had to study hard enough to receive a diploma from Harvard! 

Take the Ghosts & Gravestones Tour

Being a historic city, Boston definitely leans spooky. Maybe it’s its proximity to Salem, maybe it’s the countless ghost sightings peppering the city’s history, but Boston is one of the best cities in the country to take a ghost tour and learn as you go. Whatever you do, don't lug your roller bag through the tour (the clacking of the wheels might scare the ghost away). Drop by a Bounce luggage storage facility to stash the bags while you uncover Boston's ghoulish side. 

Take on the nerds at trivia night

If you want to test your knowledge against the best of the best, there's nothing like trivia night at a classic Boston Tavern. The city leans geeky, so you can find trivia any night of the week. There are plenty of breweries getting into the trivia game, including Aeronaut Brewing in Somerville and Remnant Brewing. The Dubliner Irish Pub, Trident Booksellers & Cafe in Back Bay, 21st Amendment in Government Center, Commonwealth Restaurant (Cambridge), and Puddingstone Tavern (Tremont Street) are classic establishments that offer trivia throughout the week.

If you're planning a trip to Boston and need a few ideas to put together an evening itinerary, there’s a lot to like in Beantown. From rooftop bars and Esplanade to trivia night at cozy pubs, the things to do at night in Boston are seemingly endless!