Boston Memorial Day Weekend 2020 – 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 2020 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

the-freedom-trail-sites-2A history buff? Immerse yourself in the glorious past of Boston with a guided stroll along the Freedom Trail.

You can choose to take a tour led by costumed re-enactors or walk the trail at your own pace.

Pay a visit to the Old South Meeting House, the Old State House Museum, the Paul Revere House, the Old North Church, and the many other historical landmarks that populate downtown Boston and the North End.

Explore American heritage on a holiday designed to commemorate our past!

Getting In: Freedom Trail Guided tour tickets – and tickets to many of the above attractions – are included with the Go Boston pass.

Check out the Art Scene

boston-museum-of-fine-artsIf you’re interested in the arts, visit the Museum of Fine Arts and explore their impressive permanent collections and exciting special exhibits.

Summer is often a time when new exhibits come into town, so be sure to check out their catalog of what’s new before you visit.

As a bonus, admission to the MFA is free on Memorial Day itself!

Looking for more art in an unconventional space? Enjoy the warm weather and the arts with a visit to the Isabella Stewart Gardner Museum: part art gallery, part historic house, part gorgeous garden. The Gardner Museum is quickly becoming a favorite among young adults for it’s beautiful synergy of art and nature.

If you’re a fan of really avant garde and contemporary art, then the ICA is a must-visit for you. Bonus: they’ve got an awesome gift store that offers Memorial Day Weekend sales.

For those of you who enjoy more indie art (or may be looking to purchase some pieces), be on the look out for the many pop-up arts festivals that occur throughout Boston, Somerville, and Cambridge throughout the summer – all of which are free to explore!

Getting In: MFA tickets, Gardner Museum tickets, and ICA tickets are included with the Go Boston pass.

Tour the City on a Trolley

CityView-Trolley-Hop-On-Hop-Off-2-Day-Pass-1If you’re just come to Boston for the first time, or if you’re a repeat visitor who’d like to see more of the city, why not check out a Boston trolley tour?

Choose a hop-on hop-off option that gives you the flexibility to decide what you want to see when, and you’re all set to explore the city at your own pace.

Staying on the trolley for the whole loop is a great way to get a comprehensive overview of the city’s top neighborhoods and attractions.

Getting In: Hop On Hop Off Boston Trolley tickets are included with the Go Boston pass.

Tour Iconic Fenway Park

Fenway Park 1Tour the legendary Fenway Park –  a thorough, behind-the-scenes tour that’s a must for any fans of baseball (or of sports in general!).

Some of the highlights you sports lovers will see on this tour include the Green Monster, Pesky’s Pole, the lone Red Seat, and more. Walk in the footsteps of Red Sox greats and really feel the history as you walk around Major League Baseball’s oldest stadium.

Insider Tip: If you’re interested in attending a game, check out the schedule while you’re in town – you can often score inexpensive tickets. Or, use your premium attraction option for a ticket through the Go Boston pass! The Red Sox do happen to be in town this Memorial Day Weekend, too.

Getting In: Fenway Park Tour tickets are included with the Go Boston pass. Select Red Sox tickets are available as a premium bonus option with the 3, 5, and 7-Day Go Boston pass.

Get Out on the Water

Charles-Riverboat-Cruise-5Soak 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.

Getting In: Charles River Cruise tickets and USS Constitution Cruise tickets are included with the Go Boston pass.

Embark on a Whale Watch

new-england-whale-watch-shutterstockYou might also consider a Boston Whale Watch, one of the most popular summer things to do in the whole city.

Sail out to Stellwagen Bank Marine Sanctuary, where you’ll find a rich feeding ground that attracts ocean creatures of all shapes and sizes.

Snap photos of the amazing wildlife that flocks to this sanctuary, from sea birds and dolphins to the magnificent whales – of which you’ll see a wide variety, too. Whale watching season lasts about six months, so be sure to see them while you can!

Getting In: New England Aquarium Whale Watch tickets are available as a premium attraction option with 3, 5 and 7-Day Go Boston pass.

Stroll the Boston Common

By Ingfbruno (Own work) [CC BY-SA 3.0], via Wikimedia Commons

By Ingfbruno (Own work) [CC BY-SA 3.0], via Wikimedia Commons

If you’d like to be outside but are on a tight budget, there are plenty of outdoor Boston activities that are just perfect things to do this Memorial Day Weekend.

Spend some time on the Boston Common or in the Boston Public Gardens. Play frisbee, pack a picnic, or just people watch! While you’re there, you can also take a brief turn on the famous Swan Boats.

During Memorial Day Weekend, the common features the Garden of Flags to commemorate Veterans.

You should also save some time to check out the street performers at Faneuil Hall and Quincy Market, who always put on a good show.

Getting In: Boston Swan Boat rides are included with the Go Boston pass.

Take a Bike Ride

Boston BikesThe start of summer is the perfect time to snag two wheels and pedal this rather bike-friendly city.

Whether you want to use your bike to get around from attraction to attraction, or prefer to leisurely explore Boston’s many beautiful parks and trails, there are plenty of options.

A favorite and long trail is the waterfront Dr. Paul Dudley White Bike Path, where you’ll also find runners and families with strollers.

If you haven’t got a bike, renting one couldn’t be easier. Rentals come with maps, helmets, and bike locks, so you’re all set to go!

Getting In: Boston bike rentals are included with the Go Boston pass.

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 starts at 3PM on May 25, 2020.

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 this year – Boston Calling.

From May 22 – 25, 2020, 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!

The information contained in this post, to the best of the author's knowledge, was accurate at time of publishing. We do our best to ensure and maintain the accuracy of this information.

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