Boston is one of the oldest cities in the United States.

Indeed, you can look forward to a wonderful time as you explore this beautiful city’s rich heritage, especially at night.

Discover the beauty of Boston as it seamlessly combines the best of the past (from its colonial history & cultural legacy) with cutting-edge technology found in some of the world’s most esteemed educational institutions.

From the stunning fine art collections to shopping at night and world-class eating & dining, there is something that will keep everyone captivated by Boston.

Here are our 19 best recommended fun things to do at night in Boston.

1/ Skywalk Observatory

For a sweeping 360-degree view of the city, head on to the Prudential Center Skywalk Observatory

Incidentally, Boston’s tallest observation deck is open to the public (since the closure of the John Hancock Tower in 2001).

Listen to a riveting narrative (also available in Japanese and French Canadian) about the city through the Acoustiguide audio tour headphones.

Shop to your heart’s content at the Shops at Prudential Center located on the first floor, where you will find Saks Fifth Avenue and Lord & Taylor.

The Skywalk Observatory is open daily until 10 pm.

Skywalk Observatory Deals | Official site

2/ Museum of Fine Arts

Your trip to Boston will not be complete without a visit to the Boston Museum of Fine Arts, which showcases one of the world’s finest art collections.

Marvel at the impressive American collection and one of the most extensive collections of Monets outside Paris.

Moreover, get to see one of the world’s most complete Degas collections.

Alternatively, peek into other cultures with Old Kingdom Egyptian and Asian collections, Japanese art, as well as Shinto and Buddhist collections.

Explore the Museum of Fine Arts daily, especially on Wednesdays to Fridays when they are open until 10 pm.

Museum of Fine Arts Deals | Official site

3/ Institute of Contemporary Art

The structure of the Institute of Contemporary Art’s exterior is a visual feast.

In particular, it resembles a remarkable folding ribbon reaching to the water’s edge.

The spacious museum was designed with the idea of viewing contemporary art from the sky downwards, and from the ground upwards.

Located in the South Boston Seaport District, its galleries feature adjustable skylights with movable ceilings and walls.

Go on a nighttime contemporary art appreciation, until 9 pm on Thursdays and Fridays.

Institute of Contemporary Art Deals | Official site

4/ Faneuil Hall Marketplace

Feel the energy of Boston at the Faneuil Hall Marketplace, which has been proclaimed as “The Cradle of Liberty in 1742.

Today, it is a thriving complex of shops, food stalls, restaurants, public spaces, and bars just a few steps away from the waterfront.

Mingle with both locals and other tourists in the cobblestone plaza to people watch and shop.

Otherwise, be entertained by the variety of street performances for your viewing pleasure.

With more than 70 retailers and 160,000 square feet of space, you will never run out of things to enjoy at this iconic festival marketplace at night.

Experience the bustling energy of the Marketplace nightly, open til 9 pm daily and until 7 pm on Sundays.

Faneuil Hall Marketplace Tours | Official site

5/ Isabella Stewart Gardner Museum

Visit the Isabella Stewart Gardner Museum to view one of Boston’s most esteemed collections of fine art.

This includes American, Asian, and European pieces featured in all media.

Check out the scheduled concerts, on-site lectures, and community events for a more enriching experience.

The museum’s history featuring a high-profile art theft will pique your interest as well.

To illustrate – it involves more than $500 million stolen including 13 valuable fine art pieces.

Indeed, this yet unsolved crime is considered to be the single most extensive private property theft ever.

On Thursdays, the museum is open until 9 pm.

Isabella Stewart Gardner Museum Deals | Official site

6/ Boston Museum of Science

Explore the wonderful world of science with the entire family at the Boston Museum of Science.

Specifically, check out over 600 interactive exhibits on dinosaurs, maps, computers, modern technology, algae, birds, and a whole lot more.

Make time for the most popular exhibits, including a world population meter, a full-sized pace capsule, a virtual fish tank, and the world’s biggest lightning bolt generator.

Don’t forget to visit the Mugar Omni Theater and the Hayden Planetarium as well!

On the other hand, you can on a nighttime scientific discovery especially on Thursdays when the museum is open until 9 pm.

Boston Museum of Science Deals | Official site

7/ Legoland Discovery Center

A trip to the Legoland Discovery Center is a treat for the whole family!

In this indoor entertainment center, adults and the younger ones can choose from 12 family activities & attractions.

For example, have fun in the Lego City Play Zone, 4D cinema, and so much more.

Enjoy The Great Lego Race VR Experience, a thrilling virtual reality experience with brick-built vehicles for a heart-pumping race against mini-figure competitors.

Before you go home, take a side trip to the retail shop offering the latest Lego products, hard to find items, and limited-edition pieces so you will have a souvenir of this awesome time in Legoland.

Have a great time at Legoland until 6 pm on Mondays; until 7 pm on Sundays, Tuesdays until Thursdays; and until 8 pm on Fridays & Saturdays.

Admission Tickets | Official site

8/ Walk the Freedom Trail

One of the best ways to explore Boston at night and see it’s attractions is to follow the Freedom Trail.

Spanning four kilometers (2.5 miles), the trail is marked with red paint or red brick on the sidewalk.

Interestingly, these markers are used to identify the stops and plaques that lead the way to the next point of interest.

Most of the sites are associated with United States colonial history, starting on the Boston Common.

As you go along the route, you will have an immersive introduction into the rich history of Boston.

Furthermore, you get to explore the distinct neighborhoods of the city.

Get up close and personal with Beacon Hill, the Old City Hall, Quincy Market, King’s Chapel, the Old Corner Bookstore, the USS Constitution Museum, and so much more.

Freedom Trail Tours | Official site

9/ Shopping

Boston has a low sales tax on retail items and no sales tax on clothing priced at below $175.

As a result, the city has become a shopper’s haven.

The shopping areas are in central locations, so you will not have a long commute for your retail indulgences.

If you are looking for luxury brands in a shopping mall or are in the mood for discount hunting in outlet stores – there is something for you within the city’s limits!

Copley Place

Get ready for some serious retail therapy at Copley Place, Boston’s top destination for high-end shopping with 75 shops sprawled on 9.5 acres.

Copley Place houses brands such as Christian Dior, Burberry, Louis Vuitton, Tiffany & Co., Neiman Marcus, and Barney’s New York.

Shops are opened til 8 pm daily, except Sunday where shops close as 6pm.

Wrentham Village

Do your shopping with huge discounts at the Wrentham Village – the outlet shopping destination to go to for  high-end, luxury designer brands in their discounted version.

Expect items to have as much as 70% off the retail price!

Over 170 stores are opened daily til 9pm, except Sunday where shops close at 6pm.

10/ Sightseeing Cruises

See the beauty of Boston from the water when you go on an unforgettable sunset cruise.

As the vessel glides leisurely on the water, enjoy your refreshing drink of choice.

Alternatively, listen to a narration about the city’s rich history and celebrated tourist attractions.

Have some snacks while gazing at the impressive city skyline at night.

Indeed, it is made even more dynamic as they start to blaze with lights along with the setting of the sun.

Feel the awesome power of the cannon fire presented off the USS Constitution, announcing the setting of the sun on a nightly basis.

The darkness provides a magical backdrop for viewing the striking Boston city skyline from the water.

Go on a memorable nighttime harbor cruise while listening to a live jazz band.

Feel yourself being transported to a bygone era – perfect for a romantic date or a relaxing time with friends.

Enjoy the gentle nighttime breeze as you enjoy your drinks out on the open air on the top deck.

Conversely, you can settle for a quieter time inside the climate-controlled cabin of the yacht.

Sunset Cruises | Night Cruises

11/ Dinner Cruises

Gaze at the splendid Boston city skyline as you enjoy a sumptuous dinner onboard a luxury ship.

Start the night with pre-dinner drinks as you sail away from the harbor.

Subsequently, view the imposing USS Constitution, the site of the Boston Tea Party, and the Bunker Hill Monument.

Sit down for a lavish buffet dinner at the ship’s elegant dining room, with live music for entertainment.

The DJ gives the music a more upbeat theme after dinner, to encourage you to get up and go straight to the dance floor!

For a more relaxed experience, you can head on to the open-air deck after dinner to enjoy the gentle breeze coming off the water.

The dinner cruises last for 2-3 hours starting at 7 pm.

Book Dinner Cruise

12/ Murder Mystery Dinner Theatre

Are you ready for a unique dinner experience?

With the Murder Mystery Dinner Theatre, you will get to participate in solving a murder mystery with the actors as part of your dining experience.

This is the largest interactive murder mystery dinner show in America.

It involves a suspect who is usually hiding in plain sight just waiting to be caught by you or one of your fellow diners.

There will never be a dull moment as you partake of delicious food, in between laughing your hearts out at the remarkable actors’ antics.

Combine your dinner with solving murder every Saturday, from 6 – 9 pm.

Book Dinner Theatre

13/ Eat Authentic Local Pizza

With hundreds of pizzerias in Boston, you can have your fill of the best pizza in America as you go on a walking night tour of the city.

This is especially true in the Little Italy area, where there are around 50 pizza places that thrive to offer mouthwatering gooey slices to hungry locals and tourists alike.

Jumpstart the tour in the historic North End neighborhood with your pizza expert where you will start with slices from three classic pizzerias to fuel around two hours of walking.

As you walk along the cobblestoned streets of Little Italy, check out the oldest pizzeria in Boston; explore the rich heritage of the neighborhoods of Charlestown, North End or Little Italy, Beacon Hill, and the Blackstone Block.

Discover historic landmarks such as the Paul Revere House, Boston’s second-oldest burial grounds, and the city’s oldest standing church.

Go for a nighttime pizza appreciation for approximately 2 hours, starting at 5 pm.

Book Pizza Tour

14/ Boston Hard Rock Café

If you are looking for a classic all-American dining experience, the Hard Rock Café Boston should not be missed.

Located next to Faneuil Hall Marketplace, this Hard Rock Café has 16,000 square feet of space.

Interestingly, it includes the restaurant that can comfortably seat 514 customers, the Rock Shop with its collectable items for sale, and the Cavern Club that features special events and live music.

Savor the flavorful dishes in a bustling atmosphere with lively music on the background to make the experience even more memorable.

Enjoy the lively Hard Rock Cafe atmosphere nightly until 11 pm on Sundays to Thursdays, and until 12 am on Fridays & Saturdays.

Book Hard Rock Cafe Dinner

15/ Visit Breweries

Boston is home to distilleries, major breweries, and several newer players in the beer brewing business.

As such, you should not be surprised if you sample some of the best beers in your life while exploring the city’s breweries in the evening, or as you indulge in a refreshing pint in one of the city’s pubs.

Sip of Boston Brewery Tour

Delve deep into the thriving Boston beer scene and go on a guided brew night tour.

Learn about the brewing process, including getting up close and personal with the equipment used.

Sample up to 12 beer kinds from three chosen cider houses distilleries, and breweries.

Evening Brewery Tour (with Dinner)

This is your chance to learn about Boston’s nanobrewing (or nano) scene, focusing on small beer-making enterprises.

The tour includes up to 15 different beer samplings, along with your dinner.

The tour includes visiting Idle Hands – the city’s first nanobrewery.

16/ Pub Crawls

Boston and beer go together, and you should definitely include a pub crawl in your night itinerary.

Majority of the drinking places were once mostly Irish pubs.

With significant changes in the cityscape, your choices now include artisanal cocktail lounges, beer bars, sports bars, nightclubs, and watering holes where you can sample the best beer choices in the country.

Fenway Pub Crawl

Indulge in local Boston brews as you go on a pub crawl in the shadow of Fenway Park.

Visit 4 baseball bars on Landsdowne St. and learn more about the Red Sox.

Enjoy local beer at each stop, and spend some time chatting with locals and fellow baseball and beer enthusiasts from all over the world.

Independence Pub Crawl

Sample local craft beer while visiting 4 historic pubs along the route of the Freedom Trail, including America’s oldest tavern.

The crawl begins at the statue of one of the Founding Fathers of the United States, Samuel Adams and proceeds to the Quincy Market and Faneuil Hall area.

17/ See Boston Ghosts

The rich, colorful history of Boston makes the city a bustling hotspot for paranormal events.

Going on a Boston ghost tour at night will give you a peek into the city’s darker side, as you listen to legends and real stories of murder, ghosts, and impossible-to-explain phenomena.

Evening Ghost Tour of Boston

Listen to stories of the most prolific crimes and of the unexplained that haunts downtown Boston as you go on a walking tour of the city’s most haunted spots.

Your tour guide will keep you riveted with Boston’s dark history, which includes the story of the Boston Massacre, the Boston Strangler.

The tour starts at 8 pm, and lasts for 1 hour and 30 minutes.

Ghosts and Gravestones Tour

Be an apprentice gravedigger for a night, with a 17th-century gravedigger as your host onboard the trolley of the doomed.

This includes a tour of two of the oldest burying grounds in the city and its occupants dating as far back as the 17th century.

18/ Photography at Night

Explore the beauty and hidden secrets of Boston at night through your camera lens with this engaging photography teaching tour.

Spend hours in the neighborhood that you wish to delve deeper into, with your knowledgeable local guide from Boston showing you the way to the most popular, scenic, and interesting spots after the sun sets.

This tour can be custom-made according to your preference, photography skills, and time frame.

Book Photography Tour

19/ Explore the Boston Common and Public Gardens

Boston Common is the oldest park in the country, and the starting point of the Freedom Trail.

Spread over 50 acres of lush greenery, the Common offers something for everyone at any given time.

For example, you can indulge in ice skating in the winter, and outdoor sports (running, tennis, baseball) during the summer.

Enjoy a leisurely stroll through the Common during the latter part of the year to be amazed at the fall foliage.

Alternatively, you can gaze at the awe-inspiring Garden of Flags on Memorial Day.

Kids will have a variety of activities and places to choose from in the Common, including a summer splash pool, a seasonal carousel, and a tadpole playground.

The public park opens daily at 6:30 am, and closes at 11 pm. However, pedestrians can access the grounds 24 hours a day.

Check Boston Common Tours

Boston is just waiting to be lovingly explored – by foot, from the water, or even from the top of an observation deck.

While the city is beautiful during the daytime, you will find it even more captivating when the darkness sets in.

Regardless of the activities at night, you will find yourself being wonderfully immersed.

Not only in the rich cultural history of Boston but also in its uniqueness and allure as a place.

Also read:

For all new cities, I go overboard on my itinerary, just to see every major attraction. Countries I've visited include New Zealand, Singapore, Hong Kong, China, Cambodia, Japan and Thailand. Mostly Asian countries. Next target - Europe!