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For fall lovers, there’s hardly anything more exciting than those first few days after the sultry summer has faded and the blustery breezes of autumn come blowing in. Everyone knows what that means… time to engage in some seriously fun fall traditions like apple-picking, pumpkin-picking, leaf-peeping, and corn-mazing!
Whether your idea of a perfect Boston day includes a solo day trip visiting museums or diving in deep for some romance with your favorite date, fall in Boston has a lot to offer visitors and Bostonians alike!
Take a Walking Tour
Summer in Boston is hot and humid, winter in Boston is chilly as chilly can be, but autumn? Autumn is absolutely glorious weather-wise and is the perfect time to go for one of the city’s spectacular walking tours.
There are walking tours that will show you some of the magnificent architecture the city is known for, walking tours that will let you sample some of the distinct flavors of the city, walking tours that will put you up close with major historical attractions, and on and on and on. Check out this guide for walking tours in Boston to pick which one is best for you!
Enjoy the Views at The Public Garden
The first botanical garden in America, The Public Garden is a lovely outdoor space that is great to visit any time of year, but as the colors change on the trees it becomes especially stunning. Take a ride in a Swan Boat and enjoy the views of the fantastic fall foliage as you are pedaled around the lagoon. There’s something about the way the late-afternoon autumn sunlight cascades across the water that just begs to be photographed, isn’t there?
September and October are two of the best months for whale-watching in Massachusetts, and Boston Harbor Cruises just happens to be one of the best whale-watching tours in the Bay State! Not only does an outing with Boston Harbor Cruises get you out to prime whale-watching locations with great educational info along the way, but the views of Boston’s skyline from the water while the leaves are changing are always a sight to see, too.
Spend an Autumn Afternoon Apple-Picking
About as quintessentially New England as an autumn afternoon can be, apple-picking at a local orchard like Honey Pot Hill Orchards is a fantastic way to spend a fall day! Honey Pot Hill Orchards is about a 45-minute drive out of the city, giving you the perfect amount of time to decompress from the hustle and bustle before pulling in at this gorgeous orchard. Pick your own apples, visit the farm animals, take a hayride, basically do all the fun fall farm things in just one autumn afternoon!
Watch the Head of the Charles Regatta
The biggest 2-day rowing race/event in the world, the Head of the Charles Regatta happens on the 3rd weekend in October and is an incredible competition to witness! The race is fun to watch from any of the spots along the 3-mile course and the festivities among the spectators are a big part of the amusement, with expos and displays from boat builders and lots of available concessions. The views of the fall foliage along the Charles River aren’t bad, either!
Get Spooked with a Ghost and Gravestones Tour
The so-called Trolley of the Doomed takes participants on a nightly 1.5-hour tour of some of Boston’s best haunts and the history behind them, so come prepared for a scare! Some notable highlights include visits to two of Boston’s most infamously haunted burial grounds, the old stomping grounds of the Boston Strangler, and graves of some of Boston’s famous figures in history, like Samuel Adams and Paul Revere. If you’re looking to be spooked, this could be perfect for you!
Take a Fall Foliage Brunch Cruise
Northern Lights departs from Boston Harbor for a 1.5-hour cruise around the Boston Harbor Islands, with views and info about the historic sites, wildlife, and lighthouses you’ll be cruising by.
A gourmet 3-course brunch is served and a bar is available so you can have your favorite adult beverage as you enjoy the expansive views of the harbor and the fabulous fall foliage that dots and decorates its shores. Delicious food, drink, and views… what more could you ask for in a scenic cruise?
Pick the Perfect Pumpkin at Pakeen Farm
Pakeen Farm is just 35 minutes southwest of the city and well worth the drive to experience their autumn offerings of hot cider, fresh mini cider donuts, and of course, pumpkin picking at their pumpkin patch! Find your perfect pumpkin for carving and soak in the peaceful farm vibes; there’s something about getting out of the city and taking in a bit of that fresh farm air that makes for a perfect fall day.
Check out the Columbus Day Parade
Switching off between the North End neighborhoods during the odd years and East End neighborhoods during the even years, the city of Boston Columbus Day Parade is a major city event featuring parade festivities like floats, entertainment, marching bands, vintage cars, and all the usual parade fun and frivolity.
Boston’s Columbus Day Parade is a celebration of Boston’s Italian heritage, so expect to see some fantastic homages to Italian history, too!
Take a Spooky Salem Day Trip
With Salem being only 45 minutes up the road and offering so much haunted history and spooky-fun activities around Halloween, you really can’t miss it! Check out the most haunted places in Salem and some of the spots Hocus Pocus filmed before going on a ghost tour or two to get in the Halloween spirit; there’s even plenty of free fun in this little haunted town! There are also lots of great restaurants and awesome places to stay in Salem (including cute little Airbnb options) if you want to make an overnight out of it, too.
Bid Adieu to Autumn at the Christopher Columbus Park Annual Trellis Lighting
Every year in late November, Boston kicks off the winter holiday season with a festive event at Christopher Columbus Park that includes entertainment, treats, giveaways, and the lighting of the iconic trellis! The Annual Trellis Lighting takes place the last week of November, ushering in the winter holiday season with over 50,000 twinkling lights.
Yes, it’s still technically fall, but twinkle lights going up all around the city will have you bidding a fond farewell to fall fun as you look forward to warm winter coziness to come!
Boston is always a cool spot to visit with tons of awesome things to do and great places to stay. You’ve got cool coffee shops, great kid-friendly activities, and Boston is even one of those places you can find plenty to do for free. Whatever time of the year you choose to visit, you won’t be bored in Boston, that’s for sure!
Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she writes alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband and cats, & drinking a maple latte.