The Best Ways to Experience Fall in Boston

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The Best Ways to Experience Fall in Boston

One of the best times to experience Boston, Massachusetts is during the autumn months when the leaves begin to change and the weather begins to cool off. There are lots of classic fall activities to do in every part of the city, but there is still more to do that you can only find in beautiful Boston. Here are our thoughts and suggestions for things you can do in and around Boston during the fall.

Do Some Whale Watching

People standing in line at a ticket booth for a ferry tour on a sunny afternoon along the Boston Harbor

One of the best times to try and catch a glimpse of a whale in Boston Harbor is during the months of September and October. If you’re patient and observant you’ll be able to see them when they come up for air, and sometimes they will even jump up out of the water so be sure to have your camera on hand. You can sometimes see the whales from the harbor pier but there are other more up close ways to look for whales. We highly recommend booking a spot on a harbor tour boat or even a tour specifically for whale watching for the best chance to see the gentle giants. Grab a jacket to protect you from the cold wind out on the harbor and keep your eyes peeled for a telltale sign of Not only will you have the chance to see some incredible wildlife, but you’ll also be able to see the incredible Boston skyline when it is dotted with red and orange trees.

Check Out Local Haunts on a Ghost Tour

Visitors to an old graveyard in Boston, MA

October is a great time of year to visit Boston, especially with Halloween just around the corner. The city is full of historical buildings and locations and there’s no telling what kind of spooky things you’ll see around town. Of course, you can pick up a walking guide map or do some of your own research to find out where to potentially catch a ghost sighting, but we suggest finding a good ghost tour to show you where the hot spots are. During October there are a lot of different ghost tours available to choose from, ranging from walking tours to trolley tours around the city. Each tour highlights the most haunted buildings and graveyards and tells you a little about their history too so you can learn while you get spooked. There are also regular historical tours available year-round for any history lovers looking to find out the less haunting side of Boston. Whether you’re interested in ghostly encounters or the scary side of Boston, a ghost tour can be a great opportunity to hear about the history that is often forgotten during the rest of the year.

Go Apple Picking

Little toddler boy picking up red apples in apple garden.

There is nothing like autumn in New England, and one of the best classic fall activities in the Boston area is apple picking. Getting out of the city and finding a local apple orchard is always a fun way to spend an afternoon. You can pack a picnic for the day or even see if there is a farmer’s market available nearby so that you can support small businesses and farmers in the area. Make sure to save space in the car for all the delicious and juicy apples you pick and maybe stop to share a few with any farm animals you meet along the way. Some orchards in the area even offer hayrides, pumpkin patches, and even corn mazes as well, so you can complete the perfect fall day all in one place. You can also get yourself a cup or two of hot apple cider in order to warm up, there are even spiked ciders available if you want to enjoy an adults-only afternoon or evening. Be sure to take in the peace and quiet and enjoy the beautiful fall weather.

Cheer for The Head of The Charles Regatta

53rd Head of the Charles Regatta in Cambridge, MA

Every year during the third week of October, Boston plays host to a massive three-day rowing event called the Head of the Charles Regatta. This is a huge race that first started in 1965 and people from all over the country and even from around the world come to participate in it. You’ll get the chance to see nearly two thousand boats compete in a number of events all along a stretch of the Charles River. While you’re not watching the events, you can browse the various fitness sponsor stalls and all the food and drink stands that are available. There’s also always boat building demonstrations which can be very interesting and informative for those who don’t know much about rowing boats or competitions. Sometimes there can be live music and performances on the riverfront for event attendees to enjoy while they cheer for their friends or family who are rowing. The lively atmosphere can make for a fun fall afternoon in Boston and offer a chance to see a cool competition with global participants.

Snap Some Fall Photography

The photo shows the Official Seal of Boston

The changing seasons bring vibrant and fiery colors to the parks and greenspaces and along the treelined streets of Boston. This time of year is an amazing opportunity to break out your camera and get some stunning fall pictures to share. The best places for photography around Boston include the Boston Common, the campus around Harvard or Cambridge, and definitely Acorn Street in Beacon Hill. Acorn Streets cobblestones and red brick homes provide a beautiful backdrop to the piles of red and orange leaves on the ground and some of the homes dress their facades for fall with pumpkins and fall greenery. You can also grab a seat on a morning or evening cruise down the Charles River and get a chance to take pictures of the treelined river during two of the most photogenic times of the day. No matter where you go around Boston, you’re sure to find excellent photo opportunities.

Take a Day Trip to Salem

Salem Massachusetts Witch Museum

Only half an hour away is the spooky town of Salem, Massachusetts. The town was made famous by the witch trials and has allowed that fame to flourish into a fun and friendly hotspot for lovers of the spooky. There is so much to do and see around Salem so you’ll definitely want to prepare to spend an entire day wandering around town and taking tours. Be sure to check out a ghost tour or even just a regular historical tour of the many homes and locations made famous during the witch trials. You can also see a few locations where the movie Hocus Pocus was filmed and stop by a few themed shops and restaurants to complete the experience. October is one of the town’s busiest times of the year and the Halloween celebrations definitely add to the experience, but you can visit Salem any time of the year and still feel a hint of the fall atmosphere.

Have you visited Boston during the fall? Share your experiences with us in the comments, we’d love to hear all about them! If you’re looking for more activities to do around Boston or if you’re just looking for how keep your Airbnb space clean and tidy, you can check our blogs for more fun and informative articles on a wide range of topics.