Best walks in Boston

Published: July 18, 2024
Public park in Boston with a walking trail

On your marks, get set... walk! That’s the way to do Boston, anyway. Unassuming, academic and full of history, this city is the ideal place to stretch your legs as it’s also very accessible, very flat, and very pretty. There’s a good mix of city lights and green spaces, and the Charles River winds serenely on its way to Massachusetts Bay offering lovely walks along the esplanade. Beware the weather – the icy wind off the Atlantic can make things pretty wet and chilly in winter – but don’t let it put you off! Fuel up on some Boston baked beans, grab your raincoat and try out one of these awesome Boston walks:

  • The Freedom Trail
  • Financial District to the Theater District
  • The Movie Mile
  • Harvard to MIT
  • The Battle Green Tour
  • The Emerald Necklace Trail

The Freedom Trail

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Many key events of the American Revolutionary War took place in Boston, and a lot of these historical sites are now accessible to visitors. To make it easy, 16 of them are connected by the 2.5-mile Freedom Trail which runs from Boston Common to Bunker Hill. It’s marked by a red path on the ground so you can’t really get lost – but if you’re finding all the history a little disorientating then use your pass to take a Freedom Trail Foundation guided tour. It covers 11 of the 16 sites on the trail, including Massachusetts State House, the USS Constitution and the site of the Boston Massacre. Your guide – complete in 18th century costume – will share all the stories of revenge and revolution so you won’t get your dates and declarations in a tangle.

The Financial District to the Theater District

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This easy walk gives you a great overview of the modern and historic side of Boston in just a couple of hours. Start at the World Trade Center bus stop and enjoy the view of the wharf and Congress Bridge before exploring the financial district. Here, as well as being able to witness Boston’s buzzing economy in motion, you’ll find the Boston Children’s Museum, the Boston Tea Party Museum, King’s Chapel and Burial Ground and the Irish Famine Memorial. Soak up the history, then go for some retail therapy at Downtown Crossing before heading towards the Theater District via Washington Street and Tremont Street. This route will take you past Chinatown, which makes a colorful diversion if you’re feeling peckish, and you’ll come out by the Shubert and Wang Theaters. From here, it’s an easy saunter to Boston Common, where you can either have a look around Emerson College Campus or just flop down on the grass and give your legs a rest.

The Movie Mile

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Many of Boston’s iconic landmarks are familiar to us because we’ve seen them so often on film and television – so why not get to know them in person? Take the Boston Movie Mile Walking Tour with Go City and discover over 30 locations you may have seen in films like Ted, Good Will Hunting and The Departed, or TV shows like Ally McBeal and Cheers. You’ll take in quiet, unassuming neighborhoods, historic homes, the original Cheers pub and the bench where Robin Williams and Matt Damon shot one of their most famous scenes. Make sure your big and small screen trivia knowledge is up to date, as your guide may just quiz you along the way!

Harvard to MIT

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This is a great walk that combines two of the city’s most famous institutions with a generous taste of student life in the city. North of the river in Cambridge, these two academic heavyweights are only a mile or so apart, but a slightly detoured route will also take you past Harvard Stadium (home of the New England Patriots until the 70s) and Harvard Business School. Explore Harvard Square on your own or join a guided tour, then head west over the Anderson Memorial Bridge towards the stadium. If you’re lucky, there might be a game going on, if not, it’s still worth a wander around. From there, turn down Harvard Way past the Baker Library to the Business School, and then circle back to the river and use the Western Avenue Bridge to cross back over. Turn left and walk along the river to Magazine Beach, then head east towards MIT. If you need more intellectual inspiration, you can take another guided tour, or check out the List Visual Arts Center.

The “Let it Begin Here” Battle Green Tour

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Take a deep dive into American Revolutionary History with a guided tour of Lexington Battle Green, included with your Go City Boston Pass. This small area is of huge historical significance, being the place where the first shots of the war were fired. See the Old Belfry that sounded the alarm, the Buckman Tavern where nervous militiamen gathered the night before the battle, the Revolutionary War Monument, the Old Burying Ground and the Henry H. Kitson Minuteman Statue. Hear stories of how the battle unfolded, George Washington’s thoughts on the whole affair, and the meaning behind the famous “Stand your ground” inscription. You’ll also see some houses and other buildings dating from the same era, so you can really feel that you’ve traveled back in time.

The Emerald Necklace walk

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A favorite among locals and visitors alike, this walk gets its name from the way it links a chain of sparkling parks and green spaces through the city. It’s a great one if you want to get away from the concrete jungle and give your legs a proper stretch – it’s around nine miles and does include some elevation, so allow up to four hours – more if you want to stop for a picnic somewhere! Start in Franklin Park – Boston’s largest, where you’ll also find the Franklin Zoo. From here, the walk takes you through the Arnold Arboretum at Harvard University, Jamaica Pond, Olmsted Park and along the Riverway to Muddy River. This route also takes you past the Isabella Stewart Gardner Museum and the Museum of Fine Arts. Continue along the long, green space that is the Commonwealth Avenue Mall all the way to the Public Garden, then either cross the suspension bridge or take the left path past the Robin Williams Memorial Bench. Finish by exploring Boston Common and be sure to take a selfie in front of Brewer Fountain!

Step it up with Go City

You can walk pretty much anywhere in Boston! Make sure you don’t miss anything with a Go City Explorer or All-Inclusive Pass and save on dozens of attractions around the city.

Karleen Stevens
Go City Travel Expert

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Things to do in Beacon Hill, Boston

Looking to spend your vacation in Boston, but not sure where to set up your home base? Why not try Beacon Hill? This affluent area of the city has plenty of things to see and do, as well as places to eat and drink. Take our word for it and read on, as we've done all the research for you! So sit back, relax and read on as we talk about the best things to do in Beacon Hill, Boston! Including: Parks Freedom Trail Walking Tour Massachusetts State House Weird gifts Dinner ideas and more! Common People Sometimes, even on vacation, you just want to relax in the great outdoors, breathing in the fresh air as birdsong fills your ears. Well, you're in Boston, so it's not like there are rolling hills of green or grandiose canyons to look upon. Instead, you'll need to go to one of Boston's great green spaces to get your fill of mother nature. Thankfully, Beacon Hill has some fantastic parks to prowl. Don't actually prowl them. You're not a cat. Firstly, why not stop by the country's oldest public park? Since the 1630s, Boston Common has been a popular destination for tourists and locals. Its 50 acres touch five of the city's main streets, two of which are in Beacon Hill. So it counts. Be sure to check out Brewer Fountain Plaza for some sweet social snaps. Or, if you like your plants more exotic and fancy stretching your legs a little bit more, Boston Public Garden is a stone's throw from the Common. The country's original botanical gardens, it's become rather famous for it swan-like boats, which many romantic comedies have used throughout the years. Besides all the amazing flora and the big swan boats, there's plenty of history to discover too, so feel free to take a guided tour if that's your thing. Or just sit down, relax, and drink it all in. Up to you. On the trail of freedom Boston's famous Freedom Trail also snakes its way into Beacon Hill. So, if you're feeling historical, curious about the nation's history, or just want to experience talking to someone in funny old-timey clothing, why not take a tour? This 90-minute, one-mile historic city tour follows Boston's world-famous red brick path. Participants will hear over 250 years of history come to life as they pass by Boston's historical sites, such as Boston Common, Massachusetts State House, Park Street Church, the Boston Massacre Site, and King's Chapel. Famous historical faces like Josiah Quincy, Henry Knox, and Phillis Wheatley will tell you their own stories and share lively anecdotes about the places, events, and drama of the American Revolution and beyond. Well, not really them. It's actors. Those guys are all long gone. If you even have just a fraction of interest in the country's independence or history, the Freedom Trail Tour is easily one of the best things to do in Beacon Hill when you visit Boston! The State of play If all the tasty history wasn't enough, why not make room for another course? Our dessert menu only has one historical item on it, a braised Massachusetts State House that's simply dripping with historical intrigue and information. The large, golden dome is visible from many parts of the city. As such, it's a beacon you should not miss. And how can you miss a beacon when you're in Beacon Hill? They offer free tours to all visitors, so why not go and learn some things? Oddities We've all been there. You're on vacation, and the expectation from your congregation is to bring them back gifts that will cause elation. But what gift do you get? Do you even know what they like? Don't worry about any of that. Go with your gut and head down to Black Ink. Inside, you'll find a world of curious oddities, from shot glasses to dinosaurs, weird baby toys to cat-themed chopstick rests. If it sounds strange and disparate, that's because it is. But it wears that randomness on its sleeve. Some of it is Boston-themed, and some of it is not. Well, it's better than a cheap postcard with a tacky tagline, isn't it? Winner winner get some dinner Let's move swiftly onto food, now. Beacon Hill has some banging restaurants to sate your well-earned hunger. These are our favs. Start your day off with a bang at Beacon Hill Bistro. Yes, it's a restaurant in a hotel, but after you've tasted their winning delights, you'll wish you had booked a room. Their crispy chicken hash with eggs is sublime, and a great way to pack your body with protein to power the day ahead. Looking for a nice lunch spot? Hit up Grotto for some classic Italian dishes with a twist. The Gnocchi with short ribs, mushrooms, and gorgonzola in a red wine sauce is something else. But they do steak too, if you're not feeling like a little Italy. For a classy dinner, fork out for No.9 Park. Diners are welcomed by a pricey tasting menu and wine pairing, as well as a dress code. No jeans and tank tops here. However, the food is as delightful as the elegant decor, with its nouveau-cuisine spin on Italian classics. Liquid Bold After all the dining and exploring, end the day with a couple of drinks. These are our picks for Beacon Hill's best boozers. For an unassuming pint or three, the Seven Ale House has you covered. Bringing some of that Boston dock attitude to this gentrified area, you can settle in for a drink and overhear the locals talking about the ball game or something. Or, enjoy the speakeasy vibe of Carrie Nation Cocktail Club. Cocktails are the name of the game here, mostly created with craft vodkas, gins, and whiskeys. Grab a couple, play a game of pool, and forget about all your troubles, if only for a few hours. And those are our picks for the best things to do in Beacon Hill, Boston! Want some more East coast goodness? Check out Boston's best museums.
Dom Bewley
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Boston Memorial Day Weekend - 10+ Fun Things to Do in May

Memorial Day Weekend is the perfect opportunity to get away and log some family time in a brand new city. To celebrate this year, pay a visit to one of the most historic cities in America - Boston! Packed with activities and events, Boston is perfect for a family-friendly weekend away. If you’re looking for Boston Memorial Day Weekend ideas, check out some of these local activities and fun things do in Boston in May, including... Walk the Freedom Trail Visit iconic Fenway Park Picnic in the Boston Common Take a Trolley Tour around town and more... Save on Attraction Admission Regular admission to a number of these attractions are included on the Go Boston pass. Choose as you go from dozens of Boston attractions & activities and save up to 55% off combined admission vs paying at the gate. See all available passes and Boston attractions – learn more. Please note, some of these special May and Memorial Day weekend events may be separately ticketed and not included on the Go Boston pass. The Freedom Trail & Other Historical Attractions Check out the Art Scene Tour the City on a Trolley Tour Iconic Fenway Park Get Out on the Water Soak up some sun this Memorial Day and discover Boston's most beloved landmarks on the Charles Riverboat Cruise -- after all, you’re in the Bay State! A scenic sail along this popular Boston waterway will escort you past top sites, as well as local sailboats, rowers, and paddleboaters. Another fun option is the USS Constitution Cruise, a delightful cruise that showcases the famed 'Old Ironsides'. This 45-minute cruise also includes informative narration of the inner harbor and a survey of popular historical and contemporary landmarks visible from the water. If you'd rather enjoy the waterfront from land, there are tons of places to catch awesome views of the ocean. Rowe's Wharf is a great place to take in the salty air and is centrally located near downtown. Embark on a Whale Watch Stroll the Boston Common Take a Bike Ride Take a Brewery Tour There are few things that say the start of summer more than a good cold beer. Tour some of the area's best local breweries for a chance to sample the new seasonal brews. Some of our favorites include Sam Adams, Harpoon, Trillium and Night Shift. If you're more into cider, you'll be pleased to find out that Downeast Cider is opening an outdoor bar in Dewey Square, near South Station. The bar opens in late May through October and will be serving up cider, beer and wine every Monday, Wednesday, Friday, and of course at the weekend. Insider Tip: If you want a free glass with your brewery tour at Sam Adams, use your Go Boston pass! Please note that the tour itself is free. Getting In: Sam Adams Brewery glassware is included with the Go Boston pass. Shop the Sales Don't forget about the shopping! Memorial Day is a time for some of the best sales of the year and Boston has no shortage of great places to shop. Head to Newbury Street, the Prudential Center, or Cambridgeside Galleria for the best shopping in town. Don't forget about all of the small businesses across the city, either! Memorial Day Parade The Somerville Veterans Memorial Parade is usually on Memorial day in May. The parade begins at Somerville City Hall and continues down Highland Ave. through Davis Sq. with the conclusion at the intersection of Holland and Broadway in Teele Sq. Getting In: This Memorial Day Parade is free and open to the public. Boston Calling Music Festival One of the most popular local music festivals falls on Memorial Day - Boston Calling. Some of the most acclaimed artists in contemporary music will come to the Harvard Athletic Complex (in Cambridge) to play to the adoring masses. It's a favorite event with locals, so tickets can sometimes go fast. For more information about line-ups and to purchase tickets, visit the event website. Getting In: Boston Calling is separately ticketed and is not included with the Go Boston pass. Remember to Save on Attraction Admission There you go - plenty of fun ideas for things to do in Boston in May to help you plan your Memorial Day weekend itinerary. Remember, many of these great ideas are included on the Go Boston pass, where you can save up to 55% on combined admission vs paying at the gate. We really hope you consider adding a few of these popular options to your upcoming plans. Enjoy!
Katie Sagal

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