Columbus Day events provide lots of entertainment throughout the 3-day holiday weekend, which always includes the 2nd Monday of October.
In 2021, Columbus Day weekend includes Saturday October 9, Sunday October 10, and Monday, October 11 – although visitors start to arrive (and hotels book up) as early as Wednesday or Thursday.
Columbus Day is an official Massachusetts state holiday, which means state offices, banks, and schools are closed, but most other places including stores and shopping malls are open.
Huge Columbus Day sales make this one of the biggest shopping weekends of the year – so keep your holiday shopping needs in mind!
Visitors fill the city – so to get the best Boston hotel rates, this is a time when you’ll want to make your reservations early.
Boston’s Columbus Day Parade – 2021
A spectacular Columbus Day Parade takes place in Boston every year. The parade includes marching brass bands, military units, Colonial militias, Italian-Boston organizations, duck boat floats, politicians, other performers, and even vintage automobiles.
During the week leading up to Columbus Day, it always occurs on the Sunday.
The parade celebrates the heritage of Italian immigrants in Boston, Christopher Columbus’s exploration of the Americas, and Massachusetts’ commitment to American freedom in the military. Fun and entertainment can be found at local organizations, military corps, politicians, performers, and marching bands of high schools.
Each odd-numbered year (2021, 2023, 2025), the parade kicks off in Boston and winds through the North End’s narrow streets – Atlantic Ave., Hanover St., Cross St.
Even-numbered years (2022, 2024), the parade marches down Bennington Street from the parking lot at Suffolk Downs to Maverick Square.
Fall Foliage Tours
Fall foliage tours are a Columbus Day tradition, as brilliant leaf colors peak around this weekend in Boston and other Southern New England locations.
You can see some of the most breath-taking color in all of New England within an hour or two of Boston – and the easiest way to view the gorgeous leaves is on a foliage tour where someone else worries about the driving!
Fall Foliage Boston Harbor Cruise on the Northern Lights
With this 2-hour afternoon sightseeing cruise around Boston Harbor during Columbus Day Weekend (and throughout October and early November), you can view colorful fall foliage as you cruise around the Boston Harbor Islands.
On Peadock’s Island and Thompson’s Island, you’ll see the brightly colored foliage, Long Island Head Light, Boston Light (America’s oldest lighthouse), Fort Warren on Georges Islands, and Fort Independence.
You can purchase beer, wine, cocktails, and other hot beverages in addition to the gourmet picnic lunch and non-alcoholic drinks included in the cost of the ticket. Let yourself be enchanted by the breathtaking scenery!
More Fall Foliage Cruises
There is no better way to enjoy this spectacular season than to take a cruise over Columbus Day weekend to see the fall foliage in New England and Canada!
Though you won’t see much color in Boston, don’t forget you can see plenty of color right in the city. There are many great places to see autumn foliage in Boston, but you should also read our suggestions for the best places to see it.
There are plenty of places to see fall foliage without leaving the city, making it a traditional Boston Columbus Day activity.
Salem is a great place to escape the city. You can also see stunning foliage, as well as Halloween decor (on display all through October), witch museums, and historical sites while visiting Salem.
Columbus Weekend Games & Concerts at TD Garden – TBD for 2021
Columbus Day weekend is a great time to catch a sporting or music event at conveniently-located TD Garden.
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Hotels near TD Garden
Cranberry Harvest Festival
The annual Cranberry Harvest Celebration, sponsored by the Cape Cod Cranberry Growers’ Association, takes place over Columbus Day Weekend when the berries are harvested from mid-September to early November.
During this festival, traditional New England activities like tours to a cranberry bog, carnival rides for the kids, food vendors, craftspeople, and fresh cranberries will be available.
As the country’s largest cranberry grower, The AD Makepeace Company hosts the festival at the company’s welcome center in Wareham, about 30 minutes south of Boston.
Plimouth Plantation and Mayflower II
Plymouth, the site of Plimouth Plantation and Mayflower II, is only about a mile from Wareham, where the Festival will be held.
The pictures recreate the Mayflower voyage of the first courageous band of English Pilgrims who landed in America in 1520, just over 100 years after Columbus arrived in the Americas.
It is as if you have time-traveled to 1620 and are among the settlers and the Wampanoag Indians who helped them survive.
Columbus Park Fall Festival
A fun fall festival will be organized by the Friends of Christopher Columbus Park on Columbus Day, with many North End and Waterfront businesses participating.
A parade for children is presented in the park at the beginning of this family-friendly festival, which includes entertainment and games for everyone.
Organize a variety of entertainment, such as magicians, storytellers, and games, to keep your event interesting.
Picnics can be enjoyed on the Greenway or take-out is available at one of the local Italian bakeries or the Food Hall in Faneuil Marketplace, just across the street.
Top October Tours
Opening Our Doors Day in Fenway
From 10:00am to 4:00pm, the Fenway Alliance presents a day of arts, culture, and educational activities that is Boston’s biggest FREE event of the year. Members will offer 60+ activities, performances, tours, and music.
Christian Science Plaza begins on Mass Ave, at the corner of Huntington Ave and Mass Ave. Children will be paraded by the Hot Tamale Brass Band, and performances will be given, along with cupcakes and activities all day long.
The Museum of Fine Arts, Isabella Stewart Gardner Museum, and Mary Baker Eddy Library Mapparium, all located in Fenway, are free to the public.
Cape Ann Artisans Open Studios
The coast of Rockport and Gloucester are stunning this Columbus Day weekend, so don’t miss the opportunity to visit artist studios! You will be able to see the wonderful works of 18 artists and artisans. They will be displaying paintings, sculptures, mosaics, photographs, pottery, and jewelry.
Boston is easily accessible by car for a day trip or for a weekend trip. You can go for walks along the beach, eat lobster dinners, and browse in local boutiques and galleries. View hotels in Rockport
October 9, 10, 11, 10am-5pm Open Studio Tour
The map and information about the Open Studio Tour is available at www.capeannartisans.com. You can also pick up maps and brochures at the Cape Ann Chamber of Commerce, the Rockport Information Booth on Route 127, or at individual studios along the tour route. Studio Tour banners are bright magenta at each location
Please contact Cape Ann Artisans at 978-546-6186 or visit their website: http://capeannartisans.com for more information.
Rob Diebboll’s “The Next Wave,” 1 Camborne Way, Rockport, is a painting by Cape Ann artist Rob Diebboll.
Boston Theater Shows on Columbus Day
- Newbury Street/Boylston Street – Great mix of designer boutiques and discount fashion – expect to see lots of “SALE” signs
- Wrentham Village – Crowds will be massive – but so will the savings!
- Assembly Row – Discount and factory outlet stores just 5 minutes (by subway) from Downtown Boston- Take the Orange Line to the Assembly Square station
- Boston shopping areas and malls – Where to shop throughout the Boston metro area
Things to Do with Kids on Columbus Day Weekend in Boston
Family-oriented activities to do with kids in Boston on Columbus Day weekend include:
- New England Aquarium – Kids and grownups alike love all the exhibits – great rainy weather choice also – plus huge Imax theater next door. Free Aquarium admission if if you have a GoBoston card, plus you go to the head of the line. More about New England Aquarium
- Boston Duck Tours – Kids’ favorite way to tour the city by land and water! More about Boston Duck Tours
- Faneuil Hall Marketplace – Bring your whole family to this popular Freedom Trail site and shopping/eating/entertainment destination – More about Faneuil Marketplace