Photo by: Belkin Family Lookout Farm

Don't tell the other seasons, but Boston is at its most beautiful in the Fall. When the cool air hits and the leaves start to turn, Boston's foliage puts on an unforgettable show that can be admired throughout the city. But, Boston's autumnal flair is attributed to far more than its breathtaking Fall views. From apple picking to spooky tours and everything in between, the Greater Boston area is the perfect place to experience Fall in all its glory. So, whether you're a local pretending to be a tourist in your own city or a visitor looking to experience an iconic New England Fall, continue reading for a curated list of the top things to do in the Greater Boston area this October!



Nothing says Fall in New England like taking a trip to a local apple orchard. Within an hour of the city, you'll discover numerous farms offering pick-your-own apples and pumpkins, hayrides, mazes, farm stands, cideries, and so many more Fall activities. You won't want to miss out on this regional tradition this October, so we've assembled a list of five local farms to check out. 


Red Apple Farm @ Boston Public Market

Location: 100 Hanover Street, Boston, MA

If you want to taste the flavors of Fall without leaving the city, stop by the Red Apple Farm stall at the Boston Public Market. Located near Boston's North End, Faneuil Hall, and the Freedom Trail, the Red Apple Farm stall at the Boston Public Market provides a convenient stop to grab fresh apples, cider donuts, and apple cider while you explore.


Brooksby Farm

Location: 54 Felton Street, Peabody, MA

Take a short trip North of the city to Peabody to visit Brooksby Farm. As you peruse their orchards, don't forget to stop by their onsite bakery to indulge on cider donuts before taking a hayride around the farm. 

Insider tip: You'll be close to Salem while at Brooksby Farm, so this is the perfect stop before attending Salem's Haunted Happenings or their Slightly Spooky Tours!


Pakeen Farm


Located just 15 minutes south of Hyde Park, Pakeen Farm is the perfect place to get pick-your-own pumpkins this October. While you visit, make sure to stop by the "Little Apple Orchard," to see Pakeen Farm's future pick-your-own apples before purchasing fresh cider and pies from the shop.


Belkin Family Lookout Farm


Some things are meant to go together- like farm-fresh hard cider, apple cider donuts, and apple picking. That's exactly what you'll find at Belkin Family Lookout Farm. Located just 20 miles west of Cambridge, Lookout Farm offers U-pick apples, a farm store, outdoor dining, and an on-site taproom. 


Nihtila Farm


Head 45 minutes south of the city to find Nihtila Farm. Not only is this an ideal place to get pick-your-own apples and pumpkins, but its location south of the city makes it a quick detour if you're heading to the Plimoth Patuxet Museums

Take a Haunted Tour

The Halloween season is big in the Greater Boston area. With some of the oldest graveyards in the country and a past steeped in U.S history, it's no surprise that the haunted tours of Boston have a story to tell. Whether you prefer to take a tour by foot or trolley, you're in for quite the scare this October! 


Freedom Trail Lantern Tour

The Freedom Trail Lantern Tour offers a first-of-its-kind experience in uncovering the grim, macabre history and mystery of the Freedom Trail! During the tour, you'll uncover the stories surrounding fatal sword duels, the grave of a ruthless pirate, scenes of scandalous murders, and the hangings of convicted witches: all real history, and all explored on the Freedom Trail. Descend into the grisly side of Boston’s iconic red-lined path by lantern light with a darkly cloaked Freedom Trail Player and bring to life true accounts of grave robbing, cold-blooded killings, and the appalling crimes of spies and assassins. This tour is recommended for visitors aged 12 and up.


Ghost City Tours of Boston

There's no question that Boston's past has left a mark on the history of the United States. But has it really made it one of the most haunted cities in the country? Ghost City Tours would say so! This October, we suggest planning a tour of our centuries-old graveyards and historic buildings to decide for yourself! From the kid-friendly The Ghost of Boston- All Ages Tour to the 21+ The Ghosts of our Father's Haunted Pub Crawl, we're sure you'll discover a walking tour that will really scare your socks off. 

Ghosts and Gravestones

Ghosts and Gravestones Trolley Tour

If you'd prefer to explore Boston's haunted history on a trolley, then the Ghost and Gravestones Tour is the one for you. Guided by a ghoulish band of the undead and a roguish gravedigger, the Trolley of Terror will go back in time as you relive grisly murders, heinous torturings, and cold-blooded executions.


Salem Haunted Happenings

If you search for the best places to celebrate Halloween in the world, chances are Salem will be on the list. Just a few miles outside of Boston, Salem's annual Haunted Happenings every October are considered by many as being the largest celebration of Halloween on earth! So, when you visit the Greater Boston area this October, don't miss out on exploring Salem during its month of celebrating the history, haunts, and magic of the area.


Salem Kids Tours

If you're venturing out with kids and still want to experience the haunted history of our area, then the Salem Slightly Spooky Tours are the perfect option for you. These tours combine true tales from Salem’s past with some mild ghost stories just for kids. 

Esplanade in Fall

Discover Fall Foliage

Did you know that Boston is considered one of the most walkable cities in the United States? That makes it the ideal place to wander in search of Fall foliage! As you explore this October, don't forget to take a moment to get out for a stroll as our trees put on one of the prettiest displays nature has to offer! Here are our recommendations for the best places in Boston to see Fall foliage:

1) The Public Garden
2) The Boston Common
3) The Esplanade
4) Beacon Hill
5) The Rose Kennedy Greenway
6) Literally the entire city!

Attend a Fall-Inspired Festival or a Sporting Event


Head of the Charles Regatta

Since 1965, the Head of the Charles Regatta has brought thousands of rowers to the Charles River to compete in the world's largest 3-day regatta! This year, more than 11,000 rowers from around the globe will compete in the 2023 Head of the Charles Regatta from October 20-22, 2023.  But the fun isn't just limited to competitors. Whether you’re a first-timer or a seasoned veteran, the Regatta offers spectators a variety of ways to experience the event.