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Residents of Boston typically flee the city during the Labor Day Weekend to Cape Cod and Martha’s Vineyard for the last holiday celebration of the summer. This makes it a great time for vacationers to visit Boston with less traffic and easier access to the attractions. Check out some of the things to do in Boston during Labor Day weekend:
Verify info of all events & locations listed. Dates & times may vary due to COVID-19.
Attractions Open Labor Day Weekend in Boston
Congress Street Bridge
Relive the single most important event leading up to the American Revolution in 1773. Interact with colonial participants from the Boston Tea Party, explore the historically restored tall ships, and experience a holographic encounter with the “Let It Begin Here” movie presentation.
All weekend explore the haunted past of Boston before the Halloween crowds start up. See some of the city’s spookiest sites, including the Omni Parker House, King’s Chapel Burying Ground and much more. Climb aboard the Trolley of the Doomed for a chilling “frightseeing” tour you’ll never forget. Visit the Ghosts & Gravestones website to learn more.
Old Town Trolley Tours of Boston has provided vacation guests and locals with more than 30 years of historic tours, news, and events. Each month the Trolley Team publishes upcoming events in Boston for visitors and residents to enjoy.
If you’re visiting during the Boston Labor Day Weekend, don’t forget to include the Old Town Trolley Tour in your itinerary. The best way to visit all the Boston attractions and historic sites in one weekend is to hop aboard Old Town Trolley when you arrive and see the best sites first. This allows you to plan your vacation around the activities that interest you and your family the most. You can hop on and off at your leisure.
If you are a Boston resident, take advantage of the Old Town Trolley Tours Hometown Pass program. After your registration is verified, you will receive free admission to the historic Boston tour each time you bring a full paying adult guest. Learn more about the Hometown Pass today.
Restaurants and Places to Eat Open Labor Day Weekend in Boston
Ned Devine’s Irish Pub is Faneuil Hall’s only restaurant and bar for modern pub dining and lively nightlife. The menu features a mix of classic Irish dishes and New England favorites like award-winning clam chowder, lobster rolls and fish & chips. Enjoy your Labor Day afternoon sipping on local beers or craft cocktails on the seasonal outdoor patio or join the vibrant nightlife crowd for live music every Friday and Saturday night.
Open on Labor Day weekend, the historic landmark pub was transformed from a long-standing neighborhood gathering spot for locals into one of Boston’s must-see stops for visitors after gaining notoriety as the location of the popular 1980’s TV sitcom, Cheers. The Cheers Pub was founded in 1969 and was discovered in 1981 by Hollywood couple Mary Ann and Glenn Charles. During their visit, they photographed the interior and exterior of the pub, which they gave to the set designer back in Hollywood to replicate for the set of the show. Cheers premiered on NBC in 1982 and remained on the air for 11 seasons, receiving over 100 Emmy nominations over the years. The pub eventually changed its name to Cheers to avoid confusion.
Anthem Kitchen & Bar is a comfortable neighborhood restaurant tucked into the heart of Boston’s historic Faneuil Hall. Gather with friends this Labor Day weekend, at the bar to share loaded short rib tots, warm potato chips, mussels, oysters, or a number of other delicious American appetizers.
Here are some insider tips on the best places to get involved with the festivities
Friday thru Monday of Labor Day Weekend
TPC Boston Norton, MA
Follow the Top 100 PGA Tour Players in the second round of the Fed Ex Cup Playoffs at the Deutsche Bank Championship. About 40 miles outside the city you can catch some of the greatest golfers in the world compete for a chance to move on to the third round of the playoffs and their chance at an $8 million prize.
The Boston Arts Festival started in 2003 to bring performing artists and interactive art exhibitions to a large public venue. The festival is scheduled for the Saturday of Labor Day Weekend with free performances all day until the fireworks celebration that evening. Christopher Columbus Park in the North End is converted into a lively cultural center complete with attractions and exhibits involving performing and visual artists. Past entertainers include dancers, theater groups, ensembles and pop music performances. Free to the public.
On Labor Day the Isabella Stewart Gardner Museum offers free admission to the public; done annually in honor of Frank Hutch, a museum trustee and Boston arts supporter. Doors open at 11am, but be sure to arrive early as once the museum is at capacity, they close their doors.
Join in on the fireworks celebration at 8:15 p.m. on the Thursday before Labor Day Weekend. The fireworks display will be along the Boston Harbor from barges anchored off the Seaport and North End to celebrate Labor Day Weekend and the beginning of fall. The best public viewing areas are the Boston Harborwalk from Piers Park, the Downtown Waterfront and Christopher Columbus Park.