Moon 52 Things to Do in Boston

THIS IS BOSTON

What comes to mind when you think of Boston? Revolutionary War history. Paul Revere. Clam chowder and baked beans. Irish bars. Baseball. Ben Affleck and Matt Damon. Busy mornings and early nights. The curious way some of the people here really do pronounce “park” and “car” without the slightest hint of an “r” in there.

But there’s more to Boston than all of that. Along the cobblestone streets you’ll find hidden local gems like the lively Rose Kennedy Greenway, art galleries in the trendy South End, and eclectic shops and restaurants in Jamaica Plain.

On the Black Heritage Trail you’ll learn about the impressive Abolitionists who called Boston home. In bustling food halls and cozy restaurants you’ll enjoy some of the best cuisine in New England. Cheering for runners on Marathon Monday or just gawking at the architecture of Beacon Hill, you’ll find friends for life. Sure, the Revolutionary War is woven throughout the city’s past and present; Bostonians cherish their history—but the city is so much more than its past.

My favorite kind of Boston day starts with a run through South Boston into Seaport and Harborwalk, then a meet-up with a friend for coffee and a croissant from a South End bakery before wandering along Newbury Street and greeting the sunset with an early cocktail. If our favorite bands are in town, my husband and I will head to one of Boston’s live music venues like the Sinclair—and all of that is just in one day.

One of the best things about Boston is its central location in New England, with a ton to explore in a relatively short distance. Spend weekends in places like the culturally rich Berkshires and LGBTQ+ proud Provincetown. Try your luck at a Connecticut casino, or hit the road for a fall foliage drive or an orchard. It’s easy to get away from the hustle of city life and get a taste of something completely different. Even a quick daytrip to Walden Pond to channel your inner Thoreau can offer a dose of much-needed respite from a busy week.

Whether you’re a born-and-bred Bostonian, a visitor, or this is where you’re planting new roots, you’ll find some of the best ways to understand the past and present that make the city iconic in this book.

TO DO LISTS

Beantown Essential

1 Root for the home team

4 Walk the Black Heritage Trail

5 Marvel at the Boston Public Library

7 Soak in sequin overload at a Jacques’ drag show

13 Rock out at the Boston Calling Musical Festival

18 Cheer on runners at the Boston Marathon

21 Taste-test chowdah

24 Customize the Freedom Trail

25 Eat Italian food on Hanover Street

Neighborhoods and City Streets

6 Feast in Chinatown

8 Explore quirky Jamaica Plain

17 Gallery hop in SoWa

25 Eat Italian food on Hanover Street

22 Splurge on Newbury Street

26 Explore Fenway beyond the Red Sox

29 Brunch around the World in the South End

32 Get to know the Boston Brahmin in Back Bay and Beacon Hill

Get Outside

9 Soak in nature at the Arnold Arboretum

14 Meander the Rose Kennedy Greenway

20 Kayak the Charles River

27 Soak up the sun on Boston’s Irish Riviera

30 Stroll on the Esplanade

33 Play at Martin’s Park

35 Get transcendental at Walden Pond

40 Go apple-picking

52 Ski and hike in the White Mountains

Drink and Dine

6 Feast in Chinatown

10 Go beyond Boston beer at a local distillery

11 Whip up a meal with professional chefs

16 Dine at a Boston food hall

21 Taste-test chowdah

25 Eat Italian food on Hanover Street

29 Brunch around the World in the South End

31 Go on a TV- and movie-themed pub crawl

41 Slurp oysters in Wellfleet

46 Taste foodie paradise in Portland, Maine

Fun for Families and Kids

2 Go whale-watching in Boston Harbor

3 Sleuth the unsolved art heist at the Isabella Stewart Gardner Museum

12 Escape to the Boston Harbor Islands

19 Geek out at the Museum of Science

23 Revisit Kennedy’s Camelot at the John F. Kennedy Presidential Library and Museum

33 Play at Martin’s Park

40 Go apple-picking

Architecture and Historic Spots

4 Walk the Black Heritage Trail

5 Marvel at the Boston Public Library

23 Revisit Kennedy’s Camelot at the John F. Kennedy Presidential Library and Museum

24 Customize the Freedom Trail

35 Get transcendental at Walden Pond

36 Go beyond Harvard Yard in Cambridge and Somerville

43 Head East on the Mohawk Trail

On the Water

2 Go whale-watching in Boston Harbor

12 Escape to the Boston Harbor Islands

20 Kayak the Charles River

27 Soak up the sun on Boston’s Irish Riviera

44 Get your feet wet at New England’s best beaches

Art and Culture

3 Sleuth the unsolved art heist at the Isabella Stewart Gardner Museum

5 Marvel at the Boston Public Library

15 See Broadway hits-to-be

17 Gallery hop in SoWa

23 Revisit Kennedy’s Camelot at the John F. Kennedy Presidential Library and Museum

38 Get inspired at Mass MoCA

Boston Parties

7 Soak in sequin overload at a Jacques’ drag show

13 Rock out at the Boston Calling Music Festival

18 Cheer on runners at the Boston Marathon

28 Go to a concert

31 Go on a TV- and movie-themed pub crawl

34 Try your luck at New England casinos

37 Celebrate Pride in Provincetown

Day Trips

35 Get transcendental at Walden Pond

36 Go beyond Harvard Yard in Cambridge and Somerville

38 Get inspired at Mass MoCA

39 Find quintessential New England in Newburyport

40 Go apple-picking

41 Slurp oysters in Wellfleet

42 Cruise Cape Cod on Old King’s Highway

43 Head East on the Mohawk Trail

48 Take in fall foliage

49 Shop local in Portsmouth, New Hampshire

Weekend Getaways

45 Visit Martha’s Vineyard

46 Taste foodie paradise in Portland, Maine

47 Sample summer in Nantucket

50 Combine foodie culture and the great outdoors in Burlington, Vermont

51 Rejuvenate in the Berkshires

52 Ski and hike in the White Mountains

1 Root for the home team

Beantown Essential • Fun for Families and Kids

It’s hard to go far in a historically Catholic city like Boston without seeing a church, but there may be no cathedrals as sacred as the temples of Gillette Stadium, the TD Garden, and Fenway Park. This trio of professional sports venues are the holy places of Boston’s other popular religions: the Patriots, the Celtics, the Bruins, and the Red Sox.

Boston has earned its nickname of “Titletown” due to an array of championship appearances and victories, with a string of World Series, Stanley Cup, NBA Finals, and Super Bowl wins in recent decades. The championship banners and trophies built one of the biggest sports fan bases in the U.S. while also creating a few, uh, jealous fans in other cities. And though Boston’s title town reputation does ebb and flow with legendary players like ex-Patriots quarterback Tom Brady coming and going, the city’s status remains steadfast in the hearts of her fans.

Whether you’ve been in Boston all your life or are a transplant with stronger ties to certain teams down in New York City or elsewhere, hearing the roar of a crowd of die-hard fans while attending one of the local team’s home games is a must-do experience.

A snowy December game at Gillette Stadium tests even the most loyal of Patriots fans (or maybe just their tolerance for cold weather), but they still show up in droves, ready to shout down Steelers and Giants fans in true Boston sports fandom style. The 65,000+ seat stadium was privately funded, and it was designed by HOK Sport who included artistic accents like a stylized lighthouse and seascape to showcase the region’s coastal history. With a massive video board in the south end zone and thoughtful seat positioning (all of which point exactly toward midfield), there’s no bad place to sit—which is good since the tickets aren’t cheap ($60 to well over $1000, www.patriots.com/tickets). Concession stands offer everything from pizza to barbeque, brats to burritos. There’s beer, too, of course. And, yes, everything is wildly overpriced. It’s unfortunate that two beers and two hot dogs can easily run you $50, but that’s about on par with most pro sports stadiums across the U.S.

The roar from TD Garden, whether in response to a slam dunk or a slap shot, is further proof of Boston’s loyal fans. Known by locals as just “the Garden,” the current arena is the second Boston Garden, this one having replaced the original in 1995. Home to both the NBA’s Celtics and the NHL’s Bruins, the Garden is a multipurpose arena with over 19,000 seats. This ten-story building has everything you would expect from a sports arena: concession stands, executive suites, private restaurants, and a giant hi-def scoreboard. Perhaps the most notable element of the Garden is the parquet flooring of the basketball court. It’s one of two arenas (the other being Orlando’s Amway Center) to use parquet, which started due to high lumber costs following World War II but stuck around as a Boston legacy. Tickets to Celtics games are about $100, and Bruins tickets are around $150 (www.tdgarden.com/events/ticket-info). In addition to being a popular sports venue, the Garden has become more of a regional draw with the arrival of the adjoining Hub on Causeway development, which opened in late 2019. The development added office and apartment towers as well as better connections between the stadium and the North Station transit hub below. There are also sports bars, a food hall, and grocery store (no, you can’t bring your own snacks inside to avoid sky-high concessions costs).

Summer games at Fenway Park are more than home runs and hot dogs—Neil Diamond’s “Sweet Caroline” is an eighth-inning mainstay that turns the whole stadium into a singalong with 38,000 of your new best friends. Of all the sports temples in Boston, Fenway reigns supreme and it’s the one that’s been around the longest. First opened in 1912, Fenway has been renovated over the years to maintain its key presence in the local (and national) sports scene: it is the oldest active major league baseball stadium in the U.S. The 37-foot left field wall—dubbed the “Green Monster” after it was painted its namesake color in 1945—is one of the stadium’s most iconic pieces of architecture. Its height prevents many homeruns from right-handed hitters, while giving those seated on top an incredible view of the entire park.

What you may not know is that Fenway Park got its name from the surrounding Fenway neighborhood rather than the other way around. The James E. McLaughlin-designed park was built to blend in with the neighborhood—a feat accomplished so well that former Red Sox pitcher Roger Clemens, upon his first visit in 1984, thought the taxi driver mistakenly dropped him off at a warehouse and not the stadium. You can expect standard ballpark fare like hot dogs, burgers, and sandwiches inside the stadium, but sports bars line the neighboring Lansdowne Street that runs the northern perimeter of Fenway. Tickets are a bit more reasonably priced, starting at $44 (https://www.mlb.com/redsox/tickets/single-game-tickets). You can also take a ballpark tour for $21.

Traffic is always a nightmare, so use public transportation when you can. Fenway Park is near the Fenway and Kenmore Green Line stops, while the Garden is above North Station, which is served by both the Orange and Green Lines as well as commuter rail from northern suburbs. Gillette Stadium has an on-site commuter rail station with service to South Station downtown, but service is infrequent. Driving is your best bet to reach Gillette, but plan to sit in hours of traffic unless you leave early both ways.

Always wear gear from the home team, prepare to spend a lot of money if you’re eating in the stadium, and plan to wait in long lines for restrooms. For winter games at Gillette, wear plenty of layers and use pocket and foot warmers to overcome the sometimes-unbearable chill. Be prepared to cheer until you’re hoarse no matter what stadium you’re in, and learn the lyrics to “Sweet Caroline” for Red Sox games—do Neil Diamond and Boston proud!

These sports venues may not have as much clout upstairs as the actual churches of Boston, but you would still be wise to follow a few commandments. Well, really just one: Thou shalt never support the Yankees.

Connect With…

26 Explore Fenway beyond the Red Sox

2 Go whale-watching

in Boston Harbor

Fun for Families and Kids • On the Water

Some of us may want to go on a whale-watching excursion because we think it’s our chance to live out a Free Willy, whale-jumping-over-our-heads fantasy. Alas, the whale theatrics in these parts aren’t quite up to Hollywood standards, but a whale-watching tour is still one of the few touristy things I repeatedly sign up for when friends or family are visiting from out of town.

The New England Aquarium partners with Boston Harbor Cruises from Long Wharf downtown, but this is a far cry from observing fish in tanks. It is an adventure to hop on a boat and head out into the Atlantic Ocean to see whales in their natural habitat. Half the fun is the anticipation of peering over the side of the boat and waiting for one of these huge, majestic sea creatures to crest above the water’s surface.

The roughly three-to-four-hour tour heads into the Stellwagen Bank National Marine Sanctuary about an hour out of the harbor to the southeast. It’s an enormous, 842-square-mile protected feeding area with an underwater plateau where deep-water currents churn up nutrients from hundreds of feet below. This attracts ocean mammals like whales and dolphins, as well as other marine life, including a variety of fish, and, yes, sharks.

You won’t see any orcas (a la Free Willy), but there is often a mix of minkes, finbacks, and humpbacks visible here. New England Aquarium naturalists provide plenty of fun facts about the creatures who live in or pass through the sanctuary—and they do a great job preparing you for photo ops.

If for some reason you don’t see a whale, tour operators will give you a free pass to return for another tour. However, I’ve gone on many of these trips and have always seen at least one or two pop up—though it sometimes takes all three or four hours to spot one. (Remember: they’re mammals and still need fresh air, even if they’re better underwater than any of us two-legged folks will ever be…save for Michael Phelps.)

While this is a kid-friendly activity, sharks do tend to come out in summer and early fall as seals move through the area. Jaws’ relatives aren’t going to jump onto the boat, but these finned predators may cause some vaguely disturbing seal-snacking gore in the water.

Plan ahead for your voyage: a windbreaker helps combat the sea breeze, occasional New England summer chill, and splashing waves. Seasickness medication is also useful for those with motion sickness. But no need pack food; most Boston Harbor Cruise vessels have a fully stocked bar and snack area with sandwiches and salads for sale.

Connect with . . .

14 Meander the Rose Kennedy Greenway

25 Eat Italian food on Hanover Street

33 Play at Martin’s Park

3 Sleuth the unsolved art heist

at the Isabella Stewart Gardner Museum

Art and Culture • Fun for Families and Kids

There are plenty of museums in town where you can gawk at beautiful paintings on the wall, but there is only one with a story as infamous as its masterpieces. In the early hours of March 18, 1990, thieves disguised as Boston Police officers gained entry into the museum, tied up the guards, and stole 13 works of art by master artists like Vermeer, Rembrandt, and Degas. In total, the art was worth $500 million, and the crime still ranks as the largest private property theft in the history of the world. The art is believed to have been offered for sale on the black market periodically since the theft; however, most leads have come up short and the case remains unsolved. Today, you’ll see evidence of the incident in the gold frames left behind in the galleries, as well as enhanced museum security. Anyone able to provide information helping to return all 13 pieces to the museum in good condition will be rewarded with $10 million.

Docents throughout the museum are able to answer questions about the robbery as well as the entire remaining collection. Visitors can also rent a $5 audio guide, narrated by the museum’s director of security, to retrace the steps of the intruders during their heist.