The 10 Best Experiences in Boston

Boston Harbour, MA
Boston Harbour, MA | © Kirkikis / Getty Images
Boston, of course, is a university town and a sports town, but it’s also so much more to its residents. While Harvard, the Massachusetts Institute of Technology and Fenway are must-see sights, make sure you also carve out time for Boston’s art, music and theater scene.

Freedom Trail Pub Crawl

If you’re a history buff or just thirsty for a pint, you’ll want to check out the Freedom Trail Pub Crawl. On this crawl, you’ll have a chance to learn about the Blackstone Block Historic District in Downtown Boston while sipping on local beers made in the greater Boston area. In addition to being the most visited spot in the city, Downtown is home to a high concentration of bars, including Union Oyster House (a National Historic Landmark building erected in the 1710s), The Bell in Hand Tavern and The Green Dragon Tavern. While you drink, you’ll be able to learn about the city around the time of the American Revolution, hear about Paul Revere’s trip through the area and learn about the specific history of Boston’s oldest watering holes.

Marshall Street on the Freedom Trail, Boston © Ian Dagnall / Alamy Stock Photo


While Boston’s Museum of Fine Arts and the Isabella Stewart Gardner Museum get most of the attention from visitors hoping to check out some of the most famous works of art, the Institute of Contemporary Art (ICA) is a not-so-hidden gem on the city’s waterfront. Featuring an oft-rotating line-up of modern art, the ICA also hosts a mix of live events, dance nights and interactive tours. Located in the city’s Seaport District, it’s an easy trek for visitors who want to stay in the Downtown area.

The Institute of Contemporary Art is on the modern side of the museum spectrum in Boston © Lane Turner / Getty Images

Boston Jazz Cruise

While crowds are light on actual beaches, the Boston Harbor is a major draw. Since the Rose Kennedy Greenway opened in 2008, the area is now a hub for restaurants, cruises and tours. With the Boston Jazz Cruise, you can get the best of all three as you set sail on a 1920s-style New England yacht combined with the sounds of jazz, provided by the Blue Motion Quartet. Grab your partner and a drink as you take in the sights of the harbor on this cruise.

Boston harbor © Vlad Ghiea / Alamy Stock Photo

Trees and trails

Lush, expansive and peaceful, the Arnold Arboretum remains one of the best-kept secrets in Boston. While it may be closer to the outskirts of the city, it’s worth a quick Uber ride into the Jamaica Plain neighborhood to check it out. Designed in 1872 by Frederick Law Olmsted, the park is the second-largest piece of what’s known as the Emerald Necklace park system. The arboretum features herbaria with over 1.3 million specimens, a huge research center and much more. Whether it’s for a picnic, some rest or to further your knowledge about trees, the arboretum has you covered.

Arnold Arboretum, Boston © hairballusa / Getty Images

Pizza and pasta in the North End

Known as Boston’s Little Italy, the North End abuts the Downtown area and the waterfront and is home to some of the best Italian food in Massachusetts. You can find everything from fresh pasta and warm pastries to delicious pizza here, and it’s all (for the most part) made in-house. Since legacy residents still live in the small Boston neighborhood, it has maintained its authenticity and homey feel throughout the years, even as new developments have sprung up nearby. As far as pizza, there’s everything from thin-crust New York-style pies like Ernesto’s to some of the best Sicilian slices in the city from bakeries like Parziale’s.

Regina Pizza, North End, Boston © Kim Karpeles / Alamy Stock Photo

Ghosts and graveyards

Being one of the first American cities in existence, Boston has a rich history and the haunted tales to go along with it. From Boston Common to the North End and waterfront, there are dozens of haunted locations in Downtown alone. You’ll hear local scary stories about criminals such as the Boston Strangler and Jolly Jane, one of the most prolific serial killers in American history. In addition, you’ll be able to tour some of the oldest burial grounds in the city, including the Granary Burial Ground, where Revolutionary leaders like Sam Adams and Paul Revere are buried. Did you know that back in the 1700s, Boston Common was the site of a public gallows?

Founded in 1660, the Granary Burying Ground is Boston’s third-oldest cemetery © Felix Lipov / Alamy Stock Photo

‘Shear Madness’ ticket

There’s a reason Shear Madness is celebrating its 40th anniversary and is currently the longest-running non-musical play in the world. A mix of improv, audience participation and murder mystery, Shear Madness lets onlookers in on the action as the cast tries to solve a murder mystery in a salon. Even if you’re not one for the theater, this play is too fun to pass up. Additionally, the show changes every night with a new ‘murderer’ being caught based on the audience’s input, questions and cues.

Red Sox game

It’s almost a cliché to list a Red Sox game on a list of best Boston activities, but where else can you see one of the oldest teams in baseball play in one of the oldest stadiums in the nation? The Fenway Frank, Bud Lights and a raucous crowd are just three of many reasons to check out a Red Sox game when you visit. In addition, Fenway Park now hosts the occasional concert, so if you’re in town at the right time, you may be able to catch Phish, Springsteen or Pearl Jam at the famous landmark.

Boston Red Sox at Fenway Park © Visions of America, LLC / Alamy Stock Photo

Blue Man Group Boston show

Entertaining, fun and genuinely bizarre, the Blue Man Group is a must-see show. A mix of circus-like stage feats and a psychedelic rock concert, the Blue Man Group is worth a trip into Boston’s theater district. While the original group grew out of New York City in 1987, Boston’s Blue Man company was one of the early adopters, and it has been running shows out of the Charles Playhouse since 1995. Highly interactive, the show also features a ‘poncho section,’ which should tell you all you need to know on that front. In addition to blowing your mind with colors and sound, the Blue Man Group is really funny – great for kids and adults alike.

The Blue Men Group performs at Charles Playhouse in Boston © Boston Globe / Contributor / Getty Images

Weaving lessons

Dahlia Popovits is a Boston legend. The long-time designer, collector and retailer ran the Dahlia Gallery on Newbury Street for more than 20 years before moving to SoWa, the arts and design district in Boston’s South End. Dahlia Gallery features handmade textiles from across the country, along with hand-woven vests and jackets created by Popovits. In addition to designing fashion, she also teaches it. In the production studio behind the showroom, she offers classes on how to weave. Popovits limits the class to four or five people so that she can give each person some one-on-one time.