Fall Activities in and Around Boston

Boston is one of America’s oldest and most beautiful cities. While Boston is charming year-round, with wonderful activities in spring, summer, and winter, fall is where Boston truly shines. There’s so much to see and do around Boston, it can be challenging to know where to start! Whether you already live in Boston, you’re planning to move here, or you’re just visiting, fall is one of the best times to visit this historical city. Here are some of our favorite autumnal activities in and around Boston. From leaf peeping to fall festivals, there’s something for everyone!

See The Changing Leaves

New England is famous for its fall foliage, and Boston has some of the most beautiful. You don’t have to leave the city to experience the amazing colors of the changing leaves. Boston’s public parks are planted with deciduous trees that put on a spectacular display every fall. We highly recommend leaf-peeping at the Boston Commons, Olmstead Park, the Back Bay Fens, and Franklin Park in the Roxbury neighborhood.

Honor the Dead at the Peabody Museum

Harvard’s Peabody Museum is wonderful to visit any time of the year, but every fall, they host a special exhibit for Dia de los Muertos, the Day of the Dead. This Mexican holiday has its roots in ancient Aztec traditions blended with Catholic beliefs. Visitors to the museum can see its ofrenda, or altar, and learn about the traditional practices, foods, artwork, and much more associated with this holiday.

Go Whale Watching

Autumn is one of the best seasons for whale watching in the Boston area. Every fall, whales pass through as they migrate to warmer waters, making them easy to spot. You’ll be likely to see humpback whales, minke whales, and harbor porpoises. Fin whales are more uncommon, and if you’re truly lucky, you might get a glimpse of the elusive and rare North Atlantic right whale. There are lots of whale-watching companies in Boston, including tours run by the New England Aquarium.

Visit Salem for Spooky Fun

Salem, Massachusetts, is best known for the witch trials that took place in 1692 and 1693. Today, the city is known for its fun, kitschy approach to all things spooky. You can walk around and go shopping in fun boutiques and tour the town’s witch-related destinations. Don’t miss the Halloween Museum and the Witch House! For extra fun, you can turn your day trip into a weekend and stay at the Hawthorne Hotel, which is supposedly haunted. Salem is only a half-hour metro train ride from Boston, or you can easily drive there.

Read On at the Boston Book Festival

The Boston Book Festival is packed with over 200 authors for a day of readings and discussions, book signings, workshops, and other lively literary events. This fun festival also has activities for the kids, walking tours, live entertainment, food trucks, the Copley Square Street Fair, and much more. And best of all? It’s completely free!

Celebrate the Harvest at Smolak Farms

Smolak Farms has been feeding and entertaining Bostonians for fifty years. Every autumn, the farm opens for apple and pumpkin picking and other harvest activities like hay rides. There are activities for the whole family! Smolak Farms is also known for its delicious food, including its famous apple cider donut ice cream. The feast doesn’t have to end when you leave the farm; you can take home some produce from their farm stand, too.

Visit A Local Brewery

There are over 100 breweries and microbreweries in the Boston area. Boston’s most famous beer is Sam Adams, which helped start the American craft beer scene, and Boston’s brewing tradition has only grown since its start. Many of these breweries offer tours and tastings. These tours are extremely popular and fun, and you might just learn a little something… or find your new favorite brew!

Note: While this is definitely an adult-oriented activity, some breweries are happy to have kids come along on the tour. Check websites or call in advance if you’ll have kids with you.

Check Out The Harbor Islands

The Boston Harbor Islands National Recreation Area is a grouping of 32 islands with public access in Boston’s Harbor. The recreation area, which is also a state park, allows you to walk a Civil War-era fort, visit historic lighthouses, explore tide pools, hike lush trails, camp under the stars, fish, and swim – although you probably don’t want to go swimming there in fall, given how cold the water will be! The Harbor Islands can be accessed by boat. There’s a public ferry, and some islands are accessible to recreational boaters, sailors, and paddlers. The park is free to visit, but the ferry does have a fee.

Pick Your Own Pumpkins

Is there anything more emblematic of the fall season than a bright orange pumpkin? When you visit a local farm, you can choose your own pumpkin and take home the perfect decoration for your hearth, doorstep, or wherever you could use a bright pop of color.

Decor isn’t all pumpkins can be! While you’re at the patch, pick up some smaller sugar pie pumpkins for baking, stewing, or turning into soup, pie, muffins, or other baked goods.

Go Hiking at Middlesex Fells

Boston is surrounded by beautiful natural areas that will make any outdoors enthusiast very happy. Just north of Boston lies one of the best hiking areas, the 2,500-acre state park called Middlesex Fells. This park features more than 100 miles of trails. The park has hikes for all levels, but the most challenging – the Skyline trail – is the most popular. The Skyline Trail includes seven miles of rough terrain, passing over hills, through wooded forests, and around stunning lakes. There’s even an observation tower to climb for unbeatable views.

Celebrate Oktoberfest

Oktoberfest is the Bavarian celebration of brewing and the harvest. It’s a very popular tradition in Germany and is beloved in the United States as well. Boston might predominantly be known as an Irish city, but the city has German roots, too. In Boston, there are several places where you can celebrate Oktoberfest with great German food, dancing, live entertainment, and of course, beer!

Go Apple Picking

New England’s fall apple crop bursts with crisp fall flavor. Apple picking in the orchards and fields surrounding Boston is a beloved tradition. It’s a delightful way to spend an afternoon. Boston orchards are home to some of the most popular apple cultivars, like McIntosh, Empire, Cortland, and Crispin apples. But if you’d like to be adventurous, go hunting for some of the unique cultivars like Sheepnose, Esopus Spitzenburg, and Pink Pearl apples.

Take a Harbor Tour

Boat tours are a fun way to see the city from a new point of view. Informative and entertaining guides will regale you with tales of the city’s history and architecture. The changing leaves make the city particularly beautiful to observe in the fall. Sunset cruises are particularly lovely as you get to watch the setting sun turn the water shades of orange to match the changing foliage.

If you plan on taking a harbor tour, you will want to bring a jacket. It can get quite cool down by the water, and the breeze can make you feel a little chilly. Consider taking a thermos of your favorite hot beverage with you!

Visit Walden Pond

Walden Pond is most famous for its association with Henry David Thoreau, who spent two years living with few possessions in a cabin on its banks. Walden Pond is in a large state reservation and has acres of woods to hike in. The pond itself is tranquil, with a mirror-like surface. It’s the perfect place to do some quiet contemplation. If you’re most interested in the Thoreau connection, you can also visit the Concord Museum, where the bed, chair, and desk from Thoreau’s cabin have been preserved.

Go “Frightseeing” At A Local Graveyard

Boston is home to some of the oldest cemeteries in the United States, and many of them are said to be quite haunted. But graveyards aren’t just a Halloween thrill; they are also a great place to learn about local history. As you’re wandering through headstones, take a moment to look and see if you can spot any familiar or famous names. If you’d like to do something more intense than a self-guided stroll, try a Ghosts and Gravestones tour. These tours are a fun, spooky way to learn about Boston’s history, culture, and residents.

Find The Best Chowder

A steaming bowl of clam chowder is the perfect food for fall. Warm and hearty, this seafood specialty is a Boston classic. But where is the best bowl of chowder? This hotly contested issue is something you should decide for yourself. Boston staples like Neptune Oyster, The Boston Sail Loft, and Ned Devine’s are known for the dish, but there are spots all over the city making this claim. Why not check out a few and decide for yourself?

Visit A Cranberry Bog

If you don’t live in New England, you might not know how cranberries grow. These unique plants are grown in flooded fields. The berries float to the top of the water and are easily harvested. Smaller growers may do a dry harvest, but big producers like Mayflower Cranberries Inc. (owned by the Ocean Spray company) and A.D. Makepeace Cranberries not only grow in bogs, they’ll let you slip on some waders and see how cranberry harvesting is really done!

Immerse Yourself in American History

A lot of America’s early history happened in and around Boston. From the Boston Tea Party and the midnight ride of Paul Revere to the first battle of the American Revolution at Lexington and Concord, Boston played an important role in the founding of our country. So too, did some of its citizens, who were early patriots, including Samuel Adams and John Hancock. Naturally, Boston is very proud of this fact and has established many monuments, museums, and an interpretive trail that will let you experience the city’s history.


Fall is the perfect time to tour Boston and learn about this history. For example, fall is a perfect time to walk Boston’s Freedom Trail. Even if you’ve lived in the city forever, there’s always something new to learn or see along this walking tour. In the fall, the weather is much more comfortable than in the summer heat. You can take it as a self-guided tour or with a professional guide. It can be a walking tour, or you can use Boston’s public transportation system to help you get around the trail.

The USS Constitution is also fun to visit in the fall. This historic ship is a museum that will tell you about naval history and the navy’s role in war and peace. It will also tell you what life on “Old Ironsides” was like when she first sailed in the 1800s. Touring the ship in the fall means shorter lines and a more pleasant experience inside and on top of the ship.

Enjoy A Picnic

Picnics might seem like a summer thing, but hear us out: fall weather is beautiful and crisp, the humidity is lower than in the summer, and there are far fewer wasps trying to share your lunch. Boston has lots of beautiful parks for picnicking. There’s the famous Boston Public Gardens, along with the parks in the Emerald Necklace. Each of these parks is home to some great picnic spots where you can enjoy a meal outdoors, people-watch, walk your dog, and enjoy the great fall weather.

We here at Boston Best Rate Movers love Boston any time of the year, and we want you to love it just as much as we do. Come visit our beautiful city in the fall – you’ll enjoy it so much you won’t want to leave! There’s so much to see and do in all seasons, and we think that fall is a truly special time here in Boston, Massachusetts.

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