27 Best Fall Activities in Massachusetts + Festivals & Foliage
🍂 Are you looking for the best Fall activities in Massachusetts to enjoy the season?
Whether you’re a local or visiting from out of town, there are plenty of amazing things to do and see. From apple-picking and leaf peeping to haunted houses and hayrides, there’s plenty to pick from in every corner of the state!
I lived in Boston for several years, and I’m still completely captivated by the colors in the fall and also just how much there is to do in this state. Plus, it’s an absolute must to visit New England in the fall at least once in your life (no, but really I’m serious!).
Today I’m sharing some of my favorite fall activities in Massachusetts – from the shores of Cape Cod to the Berkshires in Western Massachusetts. Discover what makes this season so special in The Bay State!
Greater Boston Fall Activities 🍂
As a former Bostonian, I’m slightly partial so I figured I’d start the list with some of the best ways to spend fall in or near Boston. Of course there are far too many to add here, but hopefully this gives you a good start for the best things to do during the fall.
1. Hike Middlesex Fells Reservation
Often called “The Fells” by locals, this park offers some of the best leaf peeping and hiking opportunities in the area. Just miles from downtown Boston, the 2,500 acre reservation offers dozens of trails and paths for visitors to explore. It also offers stunning views of the city skyline!
There are plenty of stunning overlooks, meadows, and even a few scenic ponds, plus lots of places to picnic or just kick back.
Whether you want a leisurely stroll or a more challenging hike, Middlesex Fells is a great destination. The best part? This is a great budget-friendly activity in Boston – admission is free!
2. Visit the Arnold Arboretum
Located in Boston’s Jamaica Plain (“JP”) neighborhood, the Arnold Arboretum is a botanical garden and research institution. Stroll through its acres of trees and plants, and witness the vibrant colors of autumn in this 265-acre urban oasis.
The Arboretum is a great place to take in the fall foliage, with over 3,000 species of plants and trees, including spectacular oaks and maples.
This is (in my opinion) easily one of the most beautiful places to visit in Boston, especially with the fall colors. Just ask the locals.
3. Take a Ghost Tour
This might not be something you think of when you hear Boston in the fall, but if you’re into spooky stuff, taking a ghost tour in Boston might just be right up your alley of fall activities in October!
There are plenty of ghost tours offered around town, but one of the most well known is this Ghosts and Gravestones tour. This tour takes you around Boston as you explore some of the darker sides of the city and visit sites that are reportedly haunted.
This tour is a great way to get into the spirit of Halloween!
Check availability & rates on this popular ghost tour!
4. See a Red Sox Game
If you’re looking for a classic fall activity in Massachusetts, look into a game at Fenway Park. The Red Sox are known to have an incredible home field advantage (like all of the city’s teams, it would seem) and the atmosphere during a baseball game is truly unbeatable!
You can buy tickets online or head to the ballpark and try to get them on the day of the game. If you can’t make a game, look into taking a tour of the field while visiting. Either way, it’s a great experience! Boston is a huge sports city so this is a great way to experience the culture, and it makes a great daytime or evening activity.
Check availability on this Fenway Park tour
5. Walk the Esplanade on the Charles
The Charles River Esplanade is a great place to spend a sunny autumn day or evening. Take a stroll along the path and take in the beautiful views of Boston’s skyline (or Cambridge) in the background. You’ll be surrounded by leaves changing all kinds of red, orange and yellow as you walk.
The Esplanade runs on the south side of the river at about 3 miles, so there is plenty of ground to cover. There are also plenty of fun stops along the way including the seasonal Night Shift Brewing beer garden that runs from the summer through October.
6. Walk through the Public Garden or “Comm Ave“
One of Boston’s best places to walk in the fall is easily the Boston Public Garden. You’ll walk through paths lined with beautiful elm trees and red maples which turn all sorts of colors. The Foot Bridge that extends over the water is also a great way to get a view of the garden and admire the foliage and surrounding city views!
Nearby Commonwealth Avenue (“Comm Ave”) is another great spot for a walk. It’s the tree lined pedestrian-only path in the middle of the road. You’ll also have beautiful brownstone homes to admire along your path (and Newbury Street is nearby as well for lots of shops & food). This is one of the most beautiful streets in Boston to walk along, and I promise you’ll love it.
7. Harpoon Octoberfest
Oktoberfest at Harpoon Brewery is a popular event and a fun fall activity for those who like to spend their day trying different beers or ciders and enjoying live music. You can also enjoy traditional German dishes like pretzels and even join in on contests.
Nearby Cambridge also has an Oktoberfest celebration, so use it as an excuse to head across the River and enjoy live music, vendors, beer gardens, and much more.
North Shore Fall Activities 🍂
Just north of Boston lies the North Shore, which has plenty of beautiful coastal towns and scenic drives to explore. Here are some of the top things to do in the North Shore for the fall.
8. Visit Salem
Probably one of the most popular or well known spots in the North Shore is Salem, Massachusetts. Salem is a great fall day trip from Boston. Known for its witchy vibes and history (the Salem Witch Trials), there’s lots to do here in the fall. There’s also a variety of foods and restaurants here, which I’ve always been impressed with when visiting!
From the Salem Witch Museum to Pickering Wharf and the surrounding shops, Salem has plenty of fun activities.
During Salem Haunted Happenings in October you’ll find spooky activities such as a witch-themed scavenger hunt, a zombie walk and an eerie haunted graveyard tour.
Pro-Tip: Salem in October is very busy – parking and hotels can be a headache!
9. Essex Coastal Scenic Byway
The Essex Coastal Scenic Byway is one of the best fall activities in Massachusetts. This 90-mile drive winds along the coast and provides some amazing views of the Atlantic Ocean, historic sites, trees changing colors and cute little scenic towns like Manchester-by-the-Sea.
The road connects about 14 different coastal towns, so make sure you stop to check out the different places along the way, from fishing villages to coastal lighthouses. It’s a great way to experience some of Massachusetts’ best scenery.
Central Massachusetts Fall Activities 🍂
Central Massachusetts is full of fall activities. Leaf peeping here in October is a must and there are plenty of scenic drives, hikes, and farms to visit where you can pick apples, pumpkins, and other seasonal treats.
10. Visit Davis Farmland and MegaMaze
Davis Farmland and MegaMaze is a great destination for families and anyone looking for the best of fall’s activities. This farm has a variety of seasonal attractions, including their world-renowned MegaMaze that features 8-acres of intricately designed pathways and plenty of frustrating dead ends.
There’s also the popular Fall Festival, which offers fun activities like great food, music, games, apple picking and more. There’s even mini golf and a 200 foot zip line that is perfect for fall and other seasons.
11. Wachusett Mountain State Reservation
Wachusett Mountain, straddling Westminster and Princeton, is another great spot to experience the crisp fall air. Hike up to the summit of the mountain and take in stunning views of central Massachusetts. Head to the ski lift for a thrilling ride up or down the mountain and unparalleled views of the autumn colors.
I’ve personally done this hike, and it’s a good hike but a lot of work for those of us who aren’t big hikers. The view is incredible though from the top, and there’s even an observation tower once you’re up there.
12. Nashoba Paddler Paddling Tours
If you’re looking for a fun, relaxing and unique activity this fall, check out Nashoba Paddler’s kayaking and canoeing tours in central Massachusetts. Located in Groton, this company offers fall foliage tours in October to experience the changing of the seasons from the river.
They also offer several other kinds of tours on the water from full moon tours to paddling with beavers! It’s a great way to explore nature and spot some of the wildlife that live near or in the water.
13. Quabbin Reservoir Loop
For a stunning scenic drive, take an unhurried drive around the Quabbin Reservoir loop. You’ll see some of Massachusetts’ most beautiful autumn landscapes as well as the shoreline of the beautiful Quabbin Reservoir that is a peaceful oasis, especially in the crisp fall weather.
This drive goes through Enfield, Hardwick, New Salem, Ware, and Belchertown, and many other places. Make sure to stop off at several of the scenic overlooks to get a better view and take pictures as you go.
South Shore, Cape Cod, & Nantucket Fall Activities 🍂
South of the Greater Boston area are plenty of spots for outdoor fun in the fall. The South Shore, Cape Cod, and Nantucket offer plenty of activities to enjoy as you take in the season’s changing beauty.
14. Wellfleet OysterFest
This celebration of all things oysters takes place for two days in late October in Wellfleet on Cape Cod. It’s a fun, family-friendly event that includes live music, fresh seafood, and lots of other exciting coastal activities.
The festival offers fun for all ages with activities like cooking demonstrations, shucking contests, and oyster-farm tours. Sample dozens of oysters as well as fresh seafood dishes served up by local vendors. OysterFest is a great fall activity for anyone wanting to explore the coastal areas of Massachusetts!
15. Nantucket’s Cranberry Festival
Every year Nantucket celebrates the Cranberry harvest and this festival is held each October. The event has grown over the years to include live music, a 5K race, a craft fair, and plenty of activities for kids. In recent years this was combined with the Island Fair, becoming known as the Harvest Fair.
The main attraction are the tours of the cranberry bogs where you can learn about the cranberry-growing process and even pick some of your own! If you’re looking for a fun, family-friendly fall activity in Massachusetts, this is it!
16. King Richard’s Faire
If you want to step back in time, King Richard’s Faire is the perfect place to do it. This annual Renaissance Festival takes place every weekend from the end of August to the middle of October. Located in Carver, Massachusetts, King Richard’s Faire is a great way to get out and enjoy the fall season.
The event is filled with jugglers, jousters, and musicians, plus a marketplace full of artisanal crafts. There are also plenty of food vendors so you won’t leave hungry.
17. Cape Cod Brew Fest
Love craft beer? The Cape Cod Brew Fest is another great event to enjoy during the fall in Massachusetts. This annual craft beer festival takes place at the Cape Cod Fairgrounds and features beers from more than 50 breweries.
Along with tasting different beers, visitors can take part in a variety of fun activities such as live music, food vendors, and interactive games.
18. Scalloping Season
Want to visit Nantucket during scalloping season? In Massachusetts, scalloping season runs from October through March, and it’s a fun way to get out on the water..
Whether you’re an experienced scalloper or a beginner, there are plenty of guides that can help you find your way around the bay. So not only will you have a chance to explore beautiful Nantucket, but you’ll also have the opportunity to harvest delicious scallops from the sea.
It’s also a great time to sample some of the scallop dishes from local restaurants!
Western Massachusetts Fall Activities 🍂
A popular destination for fall activities in Massachusetts, the western side of the state offers plenty to explore. Known especially for the Berkshires, Western Massachusetts is a great place for scenic hikes, drives and outdoor activities.
19. Jacob’s Ladder Scenic Byway
Jacob’s Ladder Scenic Byway (Route 20) is a beautiful scenic drive that takes you through 10 towns in the foothills of the Berkshires. It stretches from Lee to Russell, and along the way you’ll pass farms, homes, quaint villages and towns, old rustic barns, and plenty of scenic overlooks.
This 35 mile route offers spectacular views of the fall foliage, and it’s definitely worth veering off “the Pike” for.
20. Mohawk Trail Scenic Drive
The Mohawk Trail is a legendary scenic drive located in western Massachusetts, spanning about 69 miles. This historic route stretches from the town of Williamstown to the city of Greenfield, taking you through the picturesque Berkshire Mountains.
Originally a Native American footpath, the Mohawk Trail has a rich history that dates back centuries. Today, it is a popular tourist destination, especially during the vibrant fall season when the surrounding forests burst into a kaleidoscope of autumn colors.
As you navigate the winding roads, you’ll be treated to breathtaking rolling hills, dense forests, and charming New England towns. Along the way, you can explore a variety of attractions from state parks, hiking trails, scenic overlooks, to cultural sites.
Tip: Make sure you stop at the Bridge of Flowers in Shelburne Falls or check out Charlemont for rafting and zip lining.
21. Mount Greylock State Reservation
Looking to elevate your fall experience in Massachusetts? Oops, bad pun, but if you are, head on up to the Mount Greylock State Reservation! Whether you’re driving or hiking, this place is an absolute gem.
As the highest peak in the state, the views from the lookout are jaw-dropping. Imagine being surrounded by a panoramic view of vibrant fall colors, that’s what you’ll find. Plus, the drive up is an adventure in itself, with winding roads and stunning vistas along the way. And if you’re up for a hike, there are several trails for different skill levels.
22. Mount Sugarloaf State Reservation
Mount Sugarloaf is another great spot to enjoy the fall foliage in Massachusetts. With its stunning views of the Pioneer Valley and the Connecticut River, it’s no wonder this place is a popular destination for leaf-peepers this time of year.
From the summit, you can see miles and miles of dense forests and rolling hills blanketed with brilliant autumn colors. Whether you drive up or choose to hike to the lookout tower at the top, make sure to bring your camera along for some great fall scenery shots.
Pro-Tip: The road can be slightly narrow and the hike can be rather steep – take both into account when deciding which you prefer or can handle!
23. Six Flags Fright Fest
Looking for a good scare this fall? Then you won’t want to miss Six Flags Fright Fest – the park transforms into a spooky nightmare with haunted mazes, thrill rides and more. It’s definitely one of the best autumn activities in Massachusetts!
Be sure to wear your scariest costume and don’t forget to get a few pictures with all of the scary zombies and other ghouls you find along the way. Just remember – you’re safe during the day, but once the sun goes down… beware! So if you’re brave enough, come face your fears.
24. The Big E
The Big E in West Springfield is one of the most popular fall activities in Massachusetts! Every year, the Big E brings together delicious fair foods like fried oreos or turkey legs to unique foods like macaroni and cheese in a bread cone.
And of course you won’t just find great food, you’ll also find animal exhibits, a petting zoo, a circus, beer halls, and live music. It can be pricey, but it’s a great way to have some fun with friends or family!
Plus, it’s a great way to celebrate life in New England and what that looks like for each state. If you’re looking for a unique experience in the fall, make sure to head out to the Big E.
Fall Activities in Massachusetts 🍂
There are some favorite fall activities that span the entire state. Here’s a list of some of the best things to do during this season.
25. Hayrides
Hayrides are a classic fall activity that you can enjoy in most areas of Massachusetts. Take a hayride at any of the local farms in Massachusetts, including Connors Farm, Smolak Farms, or Verrill Farm. Hayrides are a fun way to enjoy the fall foliage and spend time outdoors with family and friends.
Sure they’re a little scratchy with the hay and all, but it’s such an essential fall activity!
26. Get Lost in a Corn Maze
Corn mazes are another fun fall activity that you can enjoy in Massachusetts. You can visit Marini Farm, Connors Farm, or Sauchuk Farm for a fun day of exploring the corn maze. Corn mazes are an engaging and interactive way to get lost (quite literally) in the fall season.
Some mazes can span up to five acres with intricate turns and pathways. With a variety of choices from short and simple to long and challenging, it’s a great activity for different ages.
27. Head to a Pumpkin Patch
No fall season is complete without a trip to the pumpkin patch. You can visit any of the local pumpkin patches in Massachusetts, including C&C Reading Farm, Parlee Farms, or Shelburne Farm. You can pick your own pumpkins, enjoy fall treats, and just take in the fall scenery.
Make sure to add pumpkin picking to your fall bucket list!
28. Apple Picking
One of the most popular fall activities in Massachusetts is apple picking. And there are so many apple orchards in the state where you can pick your own apples. Anything from Honeycrisp to Gala apples. Visit Honey Pot Hill Orchards, Russell Orchards, or Brookfield Orchards for a fun day of apple picking.
Even if you’re not into picking apples, there’s also generally apple cider donuts and apple pies available for purchase at many of these locations. Win-win, yes?
29. Wine Tasting
If wine is more your thing for the season, Massachusetts has plenty of vineyards and wineries to explore. Take a wine tasting tour and sample some of the best wines in the state. Some popular wineries to visit during the fall include:
- Nashoba Valley Winery
- Westport Rivers Vineyard & Winery
- Truro Vineyards of Cape Cod
- Plymouth Bay Winery
- Running Brook Vineyards
Final Thoughts: Best Fall Activities in Massachusetts
Fall in Massachusetts is arguably one of the most beautiful seasons in the area. It’s also a great time to explore the great outdoors and soak up all the essential fall activities. Whether you’re looking for stunning foliage, outdoor activities like hiking and apple picking, or you prefer more relaxing winery tours – Massachusetts has it.
Feel free to use the above list as a guide for all of the different fall activities in Massachusetts you can find when you’re visiting different areas in the state. The best part is that you’ll find plenty of things to do in all corners of the beautiful Bay State!
So get out there and make the most of the fall season & foliage! You can thank me later. 😉
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