New England is the quintessential fall destination in the United States, Boston is the most well-known city in New England, and October is the most popular month of the fall season. So, what we’re basically saying is—you can’t beat a fall vacation to Boston, Massachusetts, in October!
Boston, MA, has plenty of fun things to do regardless of when you visit, like the walking the Freedom Trail and exploring the Boston Public Garden. However, in October, the seasonal events and beautiful weather seem to draw tourists from near and far in droves—including the locals!
- 1 Best Things to Do in Boston in October
- 1.1 Walk the Freedom Trail
- 1.2 Get a Taste of Boston on a Food Tour
- 1.3 Watch a Sports Game
- 1.4 Explore the Boston Public Garden
- 1.5 Explore Beacon Hill
- 1.6 Grab a Beer at Oktoberfest
- 1.7 Watch the Head of the Charles Regatta
- 1.8 Head to a Pumpkin Patch
- 1.9 Go on a Haunted Ghost Tour
- 1.10 Take a Spooky Day Trip to Salem
- 1.11 Pick Apples at an Orchard
- 2 Plan Your October Trip to Boston Filled with Fall Fun
- 3 Author Bio
Best Things to Do in Boston in October
If you’re hoping for cool weather, autumn leaves, seasonal events, interesting museums, and great food during your vacation to Boston, MA, in October—you’re in luck. Boston has all these things to offer (and more!) during a fall vacation.
Keep reading to discover all the best things to do in Boston in October, so you can plan the perfect trip to New England’s favorite autumn city.
Walk the Freedom Trail
Whether your trip to Boston is planned in the fall, winter, spring, or summer—you can’t miss the chance to take a guided walking tour of the Freedom Trail in Boston!
The Freedom Trail is a 2.5-mile trail that leads you past notable sites from the American Revolution, like the Boston Common, Old South Meeting House, Boston Massacre Site, Paul Revere’s House, Old North Church, Bunker Hill, and more. Walking the Freedom Trail is especially pleasant in October since the air is crisp, cool, and refreshing, and the red brick walkways are dotted with colorful fall leaves.
Get a Taste of Boston on a Food Tour
When you think of Boston, you might think of baked beans, clam chowder, and lobster rolls. Well, there’s a good reason why. Boston is well-known for its food, and one of the best ways to get a taste of the city’s best dishes is to go on a guided food tour.
There are tons of food tours in Boston—from an Underground Donut Tour to the Bites of Boston Food Tour. However, the top-rated food tour in Boston, the North End Boston Food Tour, will not disappoint if you’d love to sample pizza, pasta, and cannoli from Boston’s “Little Italy” neighborhood. Believe us—there’s no better way to warm up on a chilly fall day than with a slice of pizza fresh out of the oven!
Watch a Sports Game
Bostonians love sports. If you’re a sports fan too, October is one of the best months to watch NFL, NHL, and MLB teams in action.
If you have a car, you can make the drive to Gillette Stadium to watch the New England Patriots face off against another NFL team. However, you don’t have to leave town to watch professional sports games. The Boston Bruins begin their hockey season in October at TD Garden, and early in the month, the Boston Red Sox are typically ending their season at Fenway Park.
Even if the Boston Red Sox aren’t playing during your vacation to Boston in October, you can still tour their iconic field, Fenway Park, on a guided walking tour. This is a must-do activity for all baseball fans visiting Boston—regardless of the month.
Explore the Boston Public Garden
The Boston Public Garden is a gorgeous location for an autumn stroll when visiting Boston in October. There are tons of sites to see here, such as the “Make Way for Ducklings” Statue, Swan Boats, George Washington Statue, and more.
In October, depending on the time of the month you’re visiting, you may be able to see the trees in the Boston Public Garden filled with vibrant red, orange, and yellow leaves. However, even if the garden hasn’t hit the “peak” for fall foliage by your trip, the garden will still be filled with lovely greenery, flowers, lakes, and other gorgeous scenery.
Explore Beacon Hill
Walking around Beacon Hill is one of the best things to do in Boston regardless of the season, but it’s especially charming in the fall.
Beacon Hill is a beautiful, historic neighborhood that overlooks the Boston Common and Boston Public Garden. It’s always stunning in every season, however, in autumn, the colorful tree-lined streets, fall flowers, and doorsteps decorated with pumpkins and mums are especially photogenic.
Don’t miss the chance to walk down (and take a photo of) Acorn Street—known as the most beautiful street in the United States. Before you begin exploring, grab a hot latte from Tatte Bakery & Cafe—one of the best coffee shops in Boston.
Grab a Beer at Oktoberfest
Oktoberfest is celebrated during the first few weeks of October in several locations across Boston, MA—but the two most popular celebrations are in Harvard Square and at Harpoon Brewery. Oktoberfest in Harvard Square includes crafts, food, music, vintage goods, parades, and five beer gardens. Harpoon Brewery’s version of Oktoberfest includes dancing, live music, and several varieties of beer.
If you can’t make it to Oktoberfest, you should at least try Samuel Adams’ Jack-O Pumpkin Ale. Samuel Adams has a taproom location across from Faneuil Hall, so it’s convenient to stop here for a pint and a bite while walking the Freedom Trail. You can also drive to Samuel Adams Boston Brewery for a guided brewery tour and beer tasting if you have a car.
Watch the Head of the Charles Regatta
The Head of the Charles Regatta (HOCR) is the largest three-day regatta in the world—and it takes place on the Charles River in Boston, MA, every October. The HOCR includes over 10,000 athletes and nearly 2,00 boats participating in over 60 events!
You can enjoy the events from several locations across the city, like the Boston University Bridge or River Street Bridge. In addition to watching the HOCR, you can also attend some of the regatta-related activities around the city, such as the Weld Exhibition, the regatta’s most popular food and drink venue, or relax at Reunion Village.
Head to a Pumpkin Patch
There are tons of pumpkin patches in the suburbs of Boston, MA, where you can go pumpkin picking in October. Shelburne Farm, Boston Hill Farm, and Hanson’s Farm are a few of the most popular.
While it might not be a good idea to pick a giant pumpkin if you need to fly home from Boston, if you’re driving home from the city, you can bring your pumpkin with you to use for fall décor or to turn into a Jack-O-Lantern!
Go on a Haunted Ghost Tour
If you’d like to discover the spooky side of Boston, consider going on the Ghosts and Gravestones Tour. This 1.5-hour nighttime tour will take you to graveyards across Boston, including Copp’s Hill Burying Ground and Granary Burying Ground. You can see the gravesites of John Hancock, Paul Revere, and Samuel Adams.
Of course, the tour wouldn’t be complete without local stories of ghosts, murder, and more in Boston. The Ghosts and Gravestones Tour is the ideal way to get in the mood for Halloween while visiting Boston in October!
Take a Spooky Day Trip to Salem
If the Ghosts and Gravestones Tour isn’t spooky enough, take a day trip to Salem, Massachusetts! Salem—the site of the infamous Salem Witch Trials in 1620—is just a 30-minute drive from Boston, making it the perfect place to visit in October.
While in Salem, don’t miss the chance to visit the Salem Witch Museum to learn about the Salem Witch Trials and Old Burying Point Cemetery to see where the victims of the trials were laid to rest. You can also snap a photo at the Salem Witch House, all decked out in fall décor, like pumpkins, and explore the witchy shops around town.
If you want to stay overnight to explore the haunted happenings in Salem for even longer, you can stay in a haunted house, like The Salem Inn.
Pick Apples at an Orchard
Old-fashioned apple picking is arguably the best way to celebrate fall during your visit to New England. There aren’t any places to go apple picking in Boston, but fortunately, Massachusetts is filled with tons of apple orchards that are just a short drive away if you rent a car during your trip to Boston.
Carver Hill Orchard in Stow, Tougas Family Farm in Northborough, and Dowse Orchards in Sherborn have plenty of apple varieties to choose from—and they are all within an hour’s drive of Boston. Plus, many of these farms and orchards also sell homemade goodies, like hand-pressed apple cider and sugary apple cider donuts, so come prepared to indulge your sweet tooth.
Plan Your October Trip to Boston Filled with Fall Fun
It’s easy to see why Boston, MA, is such a lovable (and popular) destination in October.
With no shortage of seasonal events, spooky tours, and beautiful scenery to explore during your vacation to Boston in October, you’ll find plenty of fun things to do to fill a memorable fall vacation to New England.
Brittany is a professional copywriter and founder of Travel by Brit, a travel blog that helps ordinary women dream, plan, and do extraordinary travel. She lives in Phoenix, AZ, with her husband, Michael, and golden retriever, Sedona.