Moon Boston

Neighborhood Walks, Historic Highlights, Beloved Local Spots


By Cameron Sperance

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Stroll through history, catch a game at Fenway, or snag a seat at a famous oyster bar: the best of Beantown is yours with Moon Boston.
  • Navigate the Neighborhoods: Follow one of our self-guided neighborhood walks through Back Bay and Cambridge or along the Boston Harbor
  • Explore the City: Retrace the founders’ footsteps on the Freedom Trail or peruse the works of Renoir and Van Gogh at the Boston Museum of Fine Arts. Shop the unique boutiques or designer stores on Newbury Street and wander Harvard’s picturesque campus in Cambridge. Sail out to the Boston Harbor Islands for camping and clambakes or grab a Fenway Frank and root for the Red Sox at America’s oldest ballpark
  • Get a Taste of the City: Sample oysters by the dozen or decide who has the best red sauce and cannoli in the North End. Chow down on classics like lobster rolls and “chowdah,” indulge in a Boston Cream Pie, or snack your way through a historic open-air market
  • Bars and Nightlife: Relax at a waterfront whiskey bar, chat with the bartender at a local Irish pub, or catch the game at a neighborhood sports bar. Take a sunset photo of the Boston skyline from a rooftop bar, sip on innovative cocktails, or see what’s on tap at a craft brewery
  • Local Advice: Cameron Sperance shares his expertise and love of his adopted city
  • Flexible, Strategic Itineraries, including the three-day best of Boston, a weekend with kids, day trips to Lexington and Concord, Salem, Provincetown, and more
  • Tips for Travelers including where to stay and how to navigate the T, plus advice for international visitors, LGBTQ+ travelers, seniors, travelers with disabilities, and families with children
  • Maps and Tools like background information on the history and culture of Boston, full-color photos, color-coded neighborhood maps, and an easy-to-read foldout map to use on the go
With Moon Boston’s practical tips and local insight, you can experience the best of the city.

Expanding your trip? Grab a copy of Moon New England. Hitting the road? Check out Moon New England Road Trip.



Welcome to Boston, a city on the cusp of its 400th birthday in 2030. While boldly looking forward to its future as the “new” Boston, it still warmly embraces its past—after all, this is the birthplace of the United States. Lace up a pair of comfortable shoes, grab a coffee, and meander the Freedom Trail to take in all 16 sites that commemorate the transformation of a rebellious group of colonies into a thriving global superpower.

History and higher education are Boston’s backbone. The New England city’s collegiate charm brings thousands of students to leafy campuses (and urban ones) around the metro area each fall. They are increasingly joined by a surge of new arrivals seeking employment in the region’s booming technology and health-care industries. James Beard Award-winning restaurants seem to pop up on every cobblestoned corner. Bostonians flock downtown throughout the year for beer gardens, piping hot “lobstah” rolls, food trucks, and summer concerts in the same spot that once housed never-ending traffic.

Despite its progressive vision of the future, Boston wants you to remember where it came from. From the snowy, gaslit streets of Beacon Hill to the Italian Renaissance architecture of Copley Square—and even its glassy skyline on the rise—Boston is a walk through history.

Boston Public Garden

Zakim Bridge

Boston skyline from the Harborwalk

Trillium Brewing Company beer garden

The Mapparium

Freedom Trail marker


1 Walk the Freedom Trail: Why read about history when you can walk through it? Follow the redbrick road and explore 16 key moments from the nation’s past.

2 Catch a Game at Fenway Park: Even if you don’t root, root, root for the Red Sox, the country’s oldest ballpark is worth a peek.

3 Get Inspired at Harvard University: You can’t pahk ya cah on the yahd, but it’s hard not to feel smarter after walking through the gates of the most esteemed university in the United States.

4 Stroll the Boston Public Garden: This array of seasonal plants and art installations is a must-see.

5 Wander Faneuil Hall Marketplace: The “Cradle of Liberty” is more like the cradle of shops and restaurants today. Enjoy the street performers and stick around for the nightlife.

6 Check out the USS Constitution Museum: Old Ironsides is alive and kicking—er, floating. See the ship that saved the United States.

7 Shop on Newbury Street: From vintage to couture and quirky to risqué, this street continues to be Boston’s retail mecca for all tastes, shapes, and budgets.

8 Gaze at Masterpieces at the Museum of Fine Arts: Boston’s most comprehensive museum spans French Impressionism and cutting-edge contemporary works—all under the same roof.

9 Grab a Pint: Home to Sam Adams and Cheers, not to mention numerous Irish pubs, sports bars, and new-school craft breweries, this city deserves a toast.

10 Sample Boston’s Classic Eats: Lobster rolls and Boston cream pie, red sauce and Dunkin’ Donuts . . . it’s hard to label one dish as Boston’s best, so try them all!




Any visit to Boston should start with the Freedom Trail, the city’s most popular tourist attraction. Grab a coffee and breakfast on Charles Street in Beacon Hill and wander a few blocks up Beacon Street along Boston Common, the starting point of the 2.5-mile (4-km) trail. Continue up Beacon to the gold-domed Massachusetts State House.

Following the redbrick course of the Freedom Trail will take most of the day. Stops eight and nine (Old City Hall and the Old South Meeting House) are in Downtown Crossing, an area of countless restaurants, bars, and cafés that’s a great spot to stop for lunch.

With some post-lunch pep in your step, head to the Old State House and the nearby monument to those who lost their lives in the Boston Massacre.

Old State House

PUBLIC TRANSIT: If you want to skip some stops along the Freedom Trail, the Orange Line runs from State Station (below the Old State House) to Haymarket Station and North Station, the most convenient access points for the North End.


Love it or hate it, Bostonians religiously rely on the MBTA, or the “T” as it is known to locals. The T is the oldest subway system in the United States, and because of that, it sometimes doesn’t run as well as it should—but leaders say they’re working hard to improve it. That being said, it is extremely convenient, comprehensive, and affordable compared to other systems around the country. Stop by South Station, North Station, Back Bay Station, or Downtown Crossing for on-site help with tickets and CharlieCards.

After the dose of colonial history, head up Congress Street to Boston’s City Hall. Marvel at the Brutalist architecture and then continue on the Freedom Trail into Faneuil Hall Marketplace.

After Faneuil Hall, head into the North End and Charlestown to round out the final portion of the Freedom Trail, a can’t-miss section that includes Paul Revere’s House and the USS Constitution. Be sure to save energy to return to the North End for dinner—Neptune Oyster is excellent for seafood, and any of the Hanover Street establishments are great for Italian. Dessert means making the decision between Mike’s Pastry and Modern Pastry for cannoli.

Paul Revere’s House


Hop on the Green Line to Kenmore Station and start your day with breakfast at Eastern Standard, conveniently located just above the station. Fueled up, head up Brookline Avenue to Fenway Park for an early tour of the country’s oldest ballpark. Save time for souvenir shopping along Jersey Street and to enjoy an early beer at Bleacher Bar (built directly into the stadium!) on Lansdowne Street.

You can get back on the T, but if weather permits, walk the 10-15 minutes from Kenmore Square into Back Bay along the Commonwealth Avenue Mall, a leafy green space that runs the length of the neighborhood. Depending on your mood, the Charles River Esplanade is a great waterfront retreat where you can take a break from your morning strolling and touring. Veer one block to the south, and you’ll be in the heart of shopping and dining mecca Newbury Street.

Commonwealth Avenue Mall

PUBLIC TRANSIT: Back Bay is accessible from Kenmore Square via any of the inbound Green Line trains. Take the train from Kenmore Station to Hynes, Copley, or Arlington Station.

Commonwealth Avenue eventually runs directly into the Boston Public Garden, a picturesque spot filled with the fruits of some of the city’s top greenhouses. If weather isn’t ideal, grab a drink at the Four Seasons Boston to view the park from the dry indoors.

After the Public Garden, spend the afternoon visiting the attractions of nearby Copley Square. The Boston Public Library and Trinity Church are the most popular attractions in the neighborhood, while the Prudential Skywalk Observatory is literally the top view in town.

If you continue up Huntington Avenue, you can take a Boston Duck Tour departing from the Prudential Center. After you finish, walk down Dartmouth Street into the South End for eclectic dining and drinks in Boston’s quirky, off-the-beaten-path neighborhood.

PUBLIC TRANSIT: You can also take an E-branch Green Line train from Copley Square to Prudential for an easier commute to the Prudential Center.



Boston’s tallest observation deck, the Skywalk Observatory delivers the only 360-degree view in town, from the 50th floor of the Prudential Tower (click here).


While the art inside is breathtaking, the view of Boston Harbor, downtown, and Logan Airport from the ICA’s glassy gallery is art in itself (click here).


Climb the 221 feet (67 m) to the top of this Charlestown memorial to the Revolutionary battle of the same name to get a breathtaking view of downtown (click here).


This public walkway takes you along several piers and wharves as it winds along Boston Harbor. From jumbo jets landing at Logan Airport to a skyline backdrop to your selfie, the Harborwalk knows how to shake it up (click here).

the Harborwalk


One of the largest links in Boston’s Emerald Necklace, the Arnold Arboretum gives a one-of-a-kind view of the Boston skyline from its Peter’s Hill (click here).


Start your day with a coffee—it’s hard to avoid a Dunkin’ Donuts while in town—and make your way to South Station (or any Red Line station). Take the train to Harvard University—it’s time to see the “yahd.”

An hour at Harvard Yard is enough to take in the architecture of the buildings on the university’s main campus. If you’re able to spend more time, the Harvard Art Museums and the Harvard Museum of Natural History can easily fill the rest of your morning.

Once you’re done exploring campus, plan lunch in Harvard Square. Alden & Harlow is wonderful for weekend brunch, and Harvest is a great spot for lunch any day.

After getting some neighborhood bites, be sure to take time to explore Harvard Square’s bookstores and other independent retailers. Afterward, hop back on the Red Line to South Station. Once you’re back above ground, take a stroll along the Rose Kennedy Greenway and veer over to the Harborwalk. Take in the magnificent views of Boston Harbor, and as it gets closer to sundown, pop over to the Seaport neighborhood and enjoy drinks and dinner in Boston’s newest dining destination.



Just over 40 miles (64 km) south of Boston is Plymouth, where the pilgrims landed, and its famous eponymous rock.

Visit Plymouth Rock and take a walk back in time at Plimoth Plantation, a living-history facility that lets you experience life with the Wampanoag people and the early English colonists of the 1600s. Save time for waterfront dining at a local favorite, such as Anna’s Harborside Grille, 1620 Wine Bar, or East Bay Grille.


In warmer months, hop on one of the Provincetown fast ferries (Bay State Cruises departs from the Seaport, and Boston Harbor Cruises leaves from Long Wharf downtown) in the morning and arrive on the Outer Cape in 90 minutes.

Enjoy the many galleries and eclectic shops along Commercial Street, including Cortile Gallery and Adam Peck for art, Henry & Co. for menswear, and Mate Provincetown Inc. for the best locally inspired souvenirs.

P-town has the best eating and drinking on the Cape. From dinner with a view at The Red Inn to high-end counter service on the beach at The Canteen (be sure to get a frozen rosé), you won’t be disappointed by the gourmet offerings of this town at the end of the world.


Boston may be a hub of history and higher education, but it’s a great place to bring younger travelers, too. Stay at the Hotel Marlowe in Cambridge or the Colonnade Hotel on the Back Bay/South End border in Boston for kid-friendly accommodations. The latter has a rooftop pool that is great for all ages in warmer months.


The Boston Public Market is a great foodie start to a day with children, as the numerous vendors at the food hall offer variety for all tastes and ages. After the morning nosh, stroll south down the Rose Kennedy Greenway and stop at the carousel near Faneuil Hall Marketplace. The carousel features animals native to Boston (such as the lobster and cod, as well as the skunk and harbor seal). Upon reaching Milk Street, turn left and enjoy time at Long Wharf, particularly at the New England Aquarium. The aquarium is a choose-your-own adventure attraction: You can pop in for a quick flick at the IMAX or spend a few hours watching the penguins and sea lions and vibrant marine life in the four-story Giant Ocean Tank. Take it into the wild and save time for one of the aquarium’s whale-watches, which sail daily (except in winter) from Long Wharf.

Walk the Harborwalk along Boston Harbor from the aquarium to Congress Street and turn left and cross over the Fort Point Channel. A variety of restaurants along the way are perfect for lunch, including a seasonal snack bar at the giant Hood Milk bottle outside the Boston Children’s Museum. Fueled up, you’re ready for the museum—the interactive exhibits on all levels of the facility (the nation’s second oldest of its kind) will easily take up an entire afternoon, so plan accordingly.

Boston Children’s Museum



Whether it’s a political rally, concert, Shakespeare play, or marijuana freedom rally, Boston Common draws a wide array of interests (click here).


The “Cradle of Liberty” attracts people from around the world with its street performers, bars, restaurants, and history (click here).

Faneuil Hall Marketplace


Whether it’s for the game or just to nosh on a Fenway Frank, fans of all ages head to the country’s oldest ballpark to witness sports history (click here).


Prospective students and their enthusiastic parents pour through the gates each year to tour the university and rub the statue of John Harvard for good luck (click here).


Millions of visitors (and their checking accounts) head to Boston’s retail mecca each year to shop till they drop (click here).

After wrapping up at the museum, stick around Fort Point and the Seaport for dinner, as seafood spots like The Barking Crab are fun options with outdoor seating.


Grab a coffee near North Station and take the Green Line one stop up to the Museum of Science. The 700 exhibits at the museum on the Charles River keep many a scientific mind engaged for hours. After time indoors, head outside and hop aboard Boston Duck Tours for a ride through Boston that ultimately winds up in the Charles! These amphibious vehicles get you and your family up close to all of Boston’s top attractions, including the river. Kids even get the opportunity to drive the boat while in the water.

Once you finish at the Museum of Science, you can wander over to nearby Kendall Square in Cambridge for lunch. Catalyst is a local favorite for sandwiches and other lunch staples. Afterward, hop on the Red Line to Park Street and walk up to Boston Common. On nicer days, the Common is a great spot to relax and kill time. Keep walking along the trails across Charles Street and into the Boston Public Garden. There are many ways to spend your time in the BPG, but with kids, be sure to check out the Make Way for Ducklings statue, in honor of the children’s book of the same name about a family of ducks who lived in the Public Garden. Also go on a ride on the Swan Boats, which have been city staples since 1877.

Hop on the Green Line afterward and head to Government Center. Once there, walk across City Hall Plaza to Faneuil Hall Marketplace. Stroll the cobblestones and take in the numerous street performers and vendors, which will entertain your whole brood. Afterward, do dinner in the North End. The Original Regina Pizzeria is particularly family friendly; afterward, be sure to stop by Mike’s Pastry or Modern Pastry for cannoli.

a street performer at Faneuil Hall

PUBLIC TRANSIT: All inbound Green Line trains head from Arlington Station at the Boston Public Garden to Government Center. C- and E-branch Green Line trains will go one stop farther to Haymarket, if you want to skip Faneuil Hall and go directly to the North End.


Inclement weather doesn’t have to put a damper on your visit. Thanks to the MBTA, several of the city’s top destinations are within short walks or are directly connected to the subway, preventing too much exposure to summer showers or winter blizzards.


Start your day at the Museum of Fine Arts, where its New American Café offers lunch in the museum’s expansive glass-enclosed courtyard. You can easily spend the entire morning (and well into the afternoon) exploring the special exhibitions and permanent, comprehensive collection of works ranging from the French Impressionists to profound contemporary pieces.


Grab an umbrella or your winter parka and walk three blocks to the Isabella Stewart Gardner Museum. The museum is home to the art collection of a 19th-century Boston socialite of the same name. The building’s lush indoor courtyard is a great place to pass an afternoon and ponder the mystery surrounding a still-unsolved heist at the museum. The museum’s Café G is also a fun spot for a bite before you take in more fine art.


Head back to Back Bay from the MBTA E Line, which stops directly in front of the MFA. Take the train to Prudential Station, which is built directly into the Prudential Center. Head upstairs and stop into Eataly, a 45,000-square-foot emporium of all things from the boot-shaped country in the Mediterranean. It’s a great way to shop and eat under a weatherproof roof.


Many visitors to Boston are vying to get into one of the city’s top institutions of higher education. While there are colleges spread across the city, most are found near a Green or Red Line T stop. Staying at a downtown hotel like the Omni Parker House, Godfrey Hotel, or Ritz-Carlton Boston puts you near Park Street, where the Green and Red Lines intersect.


Get an early start and take the Green Line to Boston College (BC). By taking the B branch of the Green Line, you also go through Boston University’s more urban campus on a local-style service with multiple stops. For visitors wishing for express, take the D Line to Reservoir Station and take a BC shuttle from the station directly to Boston College’s leafy, neo-Gothic campus.

Boston’s hub-and-spoke design to its train system makes it difficult to quickly travel from BC to Harvard. The 86 bus runs from Reservoir Station to Harvard Station, but Uber is usually the most efficient way to travel between the two schools. Lunch options are more prevalent in Harvard Square and will fuel you up before exploring Harvard Yard, the square, and the school’s picturesque swath of Charles River waterfront.

Take the Red Line from Harvard to Kendall Square Station. Catch a late-afternoon tour of the Massachusetts Institute of Technology (MIT) and be sure to check out the Great Dome and Killian Court. While these areas are impressive on their own, they also offer an incredible view of Boston’s Back Bay and downtown skyline from across the Charles. Having worked up an appetite, you should certainly afford time to explore Kendall Square, where a rapidly growing dining scene looks to catch the dollars of all the life science and tech companies in the area. Café ArtScience is great for the daring gourmand, while Smoke Shop proves Boston can do barbecue.

Massachusetts Institute of Technology campus


Hop into a rental car or ride-share and head to Brandeis University in Waltham for a morning tour. Reserve extra time in your day to tour the school’s Rose Art Museum, which features over 6,000 works from such names as Andy Warhol and Roy Lichtenstein. Waltham is on Route 128, and it’s just a 12-minute jaunt north to the Minute Man National Historical Park in Concord. Add this historical detour to your college trip, and plan for lunch in the suburbs.

Head back toward the city and visit Tufts University in Medford. The research university is well regarded for its international relations programs as well as its medical school in the heart of downtown Boston. Tufts is also known for its undergraduate and graduate visual arts program affiliated with the Museum of Fine Arts in Boston. Walk to nearby Davis Square in Somerville for a variety of restaurant and bar options.

Take the Red Line from Davis (if you aren’t using a car) to the JFK/UMass stop in Dorchester. Enjoy a late-afternoon tour of the University of Massachusetts-Boston, which shares a peninsula with the John F. Kennedy Presidential Library and Museum. The former commuter school is rapidly growing to include on-campus housing and is now a notable landmark along Boston Harbor. Save room for dinner at a nearby Dorchester establishment, such as Dbar.



Go for the Swan Boats and stay to enjoy the ever-changing flowers at the city’s premier and historic green thumb hub (click here).

Swan Boats at Boston Public Garden


The starting point for the Freedom Trail is also the oldest city park in the United States (click here).


What was once a congested Boston highway was buried and replaced by a linear park, the most expensive highway project in U.S. history (click here).


Channel your inner Henry David Thoreau at this popular outdoor retreat in nearby Concord, Massachusetts (click here).


Start your morning in the city’s Fenway neighborhood exploring Northeastern University,


On Sale
May 19, 2020
Page Count
300 pages
Moon Travel

Cameron Sperance

About the Author

When Cameron Sperance moved to Boston for college, he quickly fell in love with the city: its cobblestone streets, parks perfect for hanging out with a good book, and the feeling of a historic place on the move.
Today, his home is in the South End, but he loves venturing beyond his front stoop to explore quaint neighborhood markets and new restaurants, or to go for runs along the Charles River with his husband and their dog.
While he’s an avid traveler, his favorite view is of the Boston skyline as his plane, or ferry, returns home.
He’s covered every aspect of his adopted hometown for publications like the Boston Herald, Scene magazine, Stuff Boston, and Bisnow.

Learn more about this author