What I love about fall in Massachusetts is the amazing variety of things to do, and whether you’re looking for epic fall foliage, an off-season trip to the coast, breathtaking mountain views, or a cozy getaway in the woods – you can find it all in Massachusetts. Not to mention, it’s home to the most exciting Halloween destination in New England – Salem!
This post is my round-up of all the best places for fall foliage in Massachusetts, as well as the best things to do in autumn to celebrate this wonderful season. So, what are we waiting for? Let’s start planning your perfect fall getaway to the Bay State!
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Best Time To See Fall Foliage In Massachusetts
First thing’s first, if you’re looking for the best fall foliage in Massachusetts, you’ll need to know when to plan your visit. The short answer is – it depends, but generally the first two weeks of October is a safe bet for most places in Massachusetts.
For places like The Berkshires, you’ll want to plan your trip around the second week of October to try and see peak foliage, and for places around the central part of the state, the second to third week of October is ideal.
For places like Boston, and the North Shore region, including Salem, mid to late October is typically prime foliage season, and it can sometimes last through the beginning of November in these areas.
As always in all my fall posts, I like to mention that peak foliage times are never guaranteed from year to year. It’s all based on weather and temperatures throughout the year, and it can vary a bit. So these timelines are general suggestions.
Where To Go For Fall Foliage In Massachusetts
While there are more places all over the state to see amazing fall foliage, this list is my narrowed down, best-of-the-best when it comes to the most bang for your buck in terms of seeing fall color.
In no particular order, here’s where I suggest you go while leaf-peeping in Massachusetts:
1. The Berkshires
An iconic mountain region in the northwestern part of the state, The Berkshires is home to absolutely incredible fall foliage, and makes my list of the best places to visit in New England. But on top of that, it’s also a great destination for charming towns, quiet getaways, hiking, nature, and impressive restaurants. If you’re looking for a fall getaway in nature, this is the place to go.
The Berkshires also has some absolutely wonderful places to stay to make your getaway even more memorable. You can either book a cozy cabin in the woods, or stay at a variety of inns and B&B’s, ranging from traditional and homey, to modern and Instagram-worthy.
Some notable things to check out in The Berkshires in the fall season are:
→ The Mount Greylock summit, which you can drive to, or hike up
→ The Mohawk Trail scenic drive (more on both of these later, though!)
→ Drive Route 7 from Williamstown to Sheffield
→ Hilltop Orchards for cider
→ Field Farm and Sheep Hill scenic walks in Williamstown
→ The Ashuwillticook Rail Trail
Check out the “Where To Stay” section at the end for my recommendations on the best places to stay in The Berkshires!
2. Sturbridge
One of the coziest places to visit in Massachusetts during foliage season is Old Sturbridge Village, which is a recreation of a New England town in the early 1800s, and spans over 200 acres. You’ll find a covered bridge here, historic homes, and plenty of fall color to go around. For a peek at what New England life was like back in the day, this is such a wonderful experience to have (even if you’re not a history buff!).
During the fall season, they also have fun events to check starting in September, including their Harvest Fest, and their very cool Phantoms by Firelight event, which takes place on Friday and Saturday nights in October.
During Fall Fest, you’ll find all things apple at Old Sturbridge, including cider samples, apple-infused treats at their café, live music, and more. Fall Fest is just one weekend in September, so be sure to mark your calendars!
Phantoms by Firelight is the best event at OSV, however, because you can time your visit with peak foliage season. I loved my experience here in 2023, and found the ghost stories by firelight, carnival games, fire-breathing acts, and the Clues and Candy Hunt to be filled with fall spirit.
Just outside of Old Sturbridge Village, you’ll also find Sawdust Coffee & Dessert Bar, which also has fun fall drink special and delicious baked goods, as well as tree House Brewing just down the road in Charlton (spoiler alert, I talk about it later, but it’s the best brewery in New England 😉).
Sturbridge makes for a day trip, and can be reached in just over an hour from The Berkshires, and just under two hours from Boston.
3. Deerfield
Deerfield is a quaint town exploding with fall color in autumn. You can also step back in time here and visit the Historic Deerfield museum, which is home to historic buildings, and feels especially charming in the fall. Some of the houses are decorated with giant pumpkins and gourds, which is really fun to see (and also makes for the quintessential New England photo!).
Just 10 minutes outside of Deerfield, you can also visit Poet’s Seat Tower in Greenfield, which is spectacular in the fall season. You can hike or drive up, and once you arrive at the top, you’re greeted with an awesome bird’s eye view of the area dripping in fall color.
You’re also only about 25 minutes from charming Shelburne Falls, which has lovely foliage mountain views.
4. Concord
Famous for Louisa May Alcott, Walden Pond, and ties to the Revolutionary War, Concord is such a quaint little place that’s filled with serene things to do, and you guessed it … fall foliage. You’ll find lots of historic homes here as well, which just always makes you feel like you’re in the heart of New England.
Of course, Walden Pond should be at the top of your list for a fall visit. Not only will you find bright fall color surrounding the pond, it’s such a peaceful way to spend a lovely fall afternoon.
Just a few mins away from Concord in the nearby town of Lexington, you’ll also find some very festive fall things to do. The Battle Trail at the Minute Man National Historical Park is wonderful during fall foliage season. And a few minutes from that path, you can head over to Wilson Farms, which is an incredible farm store that’s especially exciting in the fall season.
5. Boston
Fall in Boston is really quite spectacular, especially if it’s a city vibe you’re after. And even though it’s an urban environment, there’s plenty of fall foliage to be had, including at the Public Gardens, Boston Common, and the Charles River Esplanade.
And what I love about autumn in Boston is that it still can feel very homey. The Beacon Hill neighborhood, especially, is filled with picturesque streets worthy of postcards, and stoops decorated with beautiful pumpkin displays.
Since Boston is also in a great location, it’s accessible to most of the places on this list, making it a great starting point for an epic New England fall road trip, or a vacation around Massachusetts in the fall.
6. Newburyport
One destination I don’t think gets enough credit in the fall season (or any season, really!) is Newburyport. I say this every time I mention this great little city, but it’s a place that feels more like a quaint town, and definitely gives you all the Hallmark movie set vibes.
Newburyport has gorgeous fall foliage, especially in its waterfront park, and Maudslay State Park. It’s also home to amazing shopping, dining, and beautiful scenery. During the fall season, they have fun events in town, and also host an awesome Oyster Fest (which I get more into later in the post!).
While exploring the North Shore, an honorable mention goes to Manchester-By-The-Sea for fall foliage, too. While small, the downtown area is very cozy, and the waterfront and harbor is bursting with stunning fall color.
7. Amherst
Between Springfield and The Berkshires, you’ll find the cute little city of Amherst, which is most famous for being the home of poet Emily Dickinson. While you can (and should!) tour her family’s homestead, there are also some really fun fall things to do around the city.
One of the best ways to enjoy fall foliage in Amherst is to bike one of the rail trails, and I especially love the Norwottuck Rail Trail. This 11-mile paved trail is pretty flat, making it great for all skill levels, and takes you over a beautiful bridge offering river views backdropped by foliage, and through other scenic areas.
Another great rail trail nearby is the Manhan Rail Trail, which is in Easthampton. This one is also great for foliage color along the path.
Mount Holyoke Range State Park, is another wonderful foliage place to check out in Amherst, and offers plenty of trails to explore for a day out in nature.
You’ll also be able to find all kinds apple orchards nearby in this area, and explore the cute little downtown area for shops and restaurants.
8. Ipswich
I think Ipswich is another underrated destination in New England, and it also boasts amazing fall color this time of the year. Ipswich is often regarded as a coastal town, but it has such beautiful farm lands and parks to explore, making this a great place to visit in the fall, too. It’s also only about 30 minutes from Salem, if you’re looking for a day trip to take from there.
Two of my favorite places to visit in the fall in Ipswich are Russell Orchards and Appleton Farms, and they’re only 10 minutes apart from one another. Appleton Farms is owned by the Trustees, and is one of the oldest continually-operating farms in the entire country. Here, you’ll find picturesque rural scenery that’s worthy of a postcard, and miles of walking trails that are ablaze with fall color. They also have a cute little farm store to shop from before you leave.
Russell Orchards is part winery and part farm store, and 100% worth a stop! In the fall season, you can pick your own apples, and get some cider doughnuts from their bakery. They also have all kinds of fall treats and decorations available, like pumpkins, gourds, mums, ice cream and local products. Be sure to swing by their winery for a tasting, too!
Also in Ipswich, you can tour the gorgeous Crane Estate, visit the Wolf Hollow sanctuary, and sip on seasonal crafts brews at True North Ale Company.
9. Quabbin Reservoir – A Hidden Gem!
One foliage spot in Massachusetts that not as many people know about is the Quabbin Reservoir. And man, the fall color here is amazing! This reservoir is the largest body of water in Massachusetts (besides the coastline, of course), and is one of the biggest suppliers of unfiltered water in the entire country.
During your visit, you have access to over 100 miles of scenic trails here that are perfect for walking and biking, as well as awesome overlooks to enjoy the scenery from different perspectives.
Quabbin Reservoir is located pretty much smack dab in the middle of state, so it’s easy to make a day trip here from most places mentioned in this post, or to incorporate into your fall itinerary while touring Massachusetts.
Best Things To Do In The Fall In Massachusetts
Okay, now that we have my favorite fall foliage destinations out of the way,
let’s get into all the most fun things to do in Massachusetts in the fall season!
10. Visit Salem In October
I mean, this is a given, right?
Not that it needs an introduction, but I do think that experiencing Salem in October is something everyone in New England should do at least once. I’m not especially big into Halloween (I love fall, but I’m mostly into Halloween for the candy 😉), but even I kind of love Salem during the month of October.
Between spooky ghost tours, the Salem Witch Trials Memorial, Hocus Pocus filming locations, Halloween events during Haunted Happenings, wonderful restaurants, tons more history, and New England charm everywhere, Salem is really the perfect October experience to have in Massachusetts.
Pro Tips For Visiting Salem in October:
→ It’s going to be crowded. This was a shock to me the first time I went in October (not sure why, exactly!). But book well in advance, make dining reservations ASAP, and anticipate lots and lots of people everywhere.
→ If you’re in Boston, or staying in Boston, I love to recommend this Boston to Salem ferry. It takes less than an hour, and it saves you the hassle of finding parking in Salem. This is especially handy on the weekends.
→ Salem fall foliage is usually and its best closer to mid-late October, which perfectly coincides with Halloween festivities!
Psst! I have some helpful guides including planning the perfect Salem, MA day trip, and the best time to visit Salem if you need more information 😉
11. Drive The Mohawk Trail
The Mohawk Trail is one of the most, if not the most, scenic drives in all of Massachusetts during the fall season. Located in The Berkshires region, this drive begins in Williamstown, ends in Greenfield, and spans over 60 miles of gorgeous views.
The drive also stops by some of the best towns to visit in The Berkshires area, including Shelburne Falls and North Adams. And what I love about this drive is that there are so many things to do along the way, including awesome breweries, cideries, coffee places, restaurants, and plenty of scenic overlooks where you’ll want to have your camera ready.
One of the best places for incredible views is the Whitcomb Summit, which is the highest point along the route. Be sure to stop here to take in all the gorgeous fall color!
12. Have A Cozy Cabin Getaway
The Berkshires is also the best destination in Massachusetts for a cozy cabin getaway, which just feels especially perfect once the chilly fall weather sets in. And this region has so many wonderful cabins and places to rent that you’re sure to find the perfect one for you.
Whether you’re hoping for small place that’s a romantic hideaway for two, or a bigger retreat for a family gathering, there’s definitely a little something for everyone.
And with The Berkshires, you’re never too far away from a cute town with great farm-to-table dining, or a relaxing, scenic hike. So, pick whichever house calls to you, and then take things from there.
🍁 Click here to browse the best places for a fall foliage Berkshires escape
13. Enjoy The Foliage Views From A Mountain Peak
There are some awesome mountain peaks in Massachusetts that offer incredible views year-round, but are especially epic in the fall season with foliage colors.
The Mount Greylock summit in The Berkshires is one of the best to check out, as it’s the highest point in the entire state. You can choose to either hike to the top, or drive the auto-road up, and from the summit, you can see 90 miles in the distance on a clear day. It’s been a minute since I’ve done this hike, but man, I do remember it as being incredible!
Mount Holyoke is another great summit to experience in the fall, and also offers both an auto road, and hiking trails to get to the top.
14. Stock Up At A Fall Market Or Stand🍁🍎
One of my personal favorite things to do in the fall in New England is visit all the amazing fall markets and stands, and Massachusetts is home to some of the best. Well, every New England state has some pretty great ones, so let’s instead say that Massachusetts is no exception 😉
My two favorites in Massachusetts are Wilson Farms in Lexington, and Cider Hill Farm in Amesbury.
Wilson Farms is easy to visit if you’re planning a trip to Concord or Lexington. This market is open year-round, but in the fall, they place hundreds of pumpkins in crates in front of their main entrance, and just that alone gives you all the fall vibes you’re hoping for. But inside, the market is impressive, and you can spend a lot of time here filling your basket with all kinds of local produce, specialty foods, and goodies.
In Amesbury, Cider Hill Farm is perfect if you’re visiting Newburyport, as it’s only about 15 minutes away. This is a true fall destination, and they have pick your own apples and pumpkins, hard cider, regular cider, cider donuts, an incredible farm store, animals, ice cream and so much more. It’ll be heard to leave!
15. Attend A Farmhouse Wood-Fired Pizza Picnic At Appleton Farms
Remember earlier in the post when I raved about Ipswich being a fun fall destination? Well, their wood-fired pizza picnic events are one of the reasons why! These events actually take place all summer, too, but they continue through all of October, making this something to check out this fall season.
Pack up some lawn chairs and a picnic blanket, throw on your coziest sweater, and head to the farm for some amazing wood-fired pizza. They also offer more yummy foods prepared by the farm’s kitchen. Then, enjoy your hand-crafted pizza overlooking all the beautiful fall colors, and savoring the perfect fall day!
These events take place every Friday, Saturday and Sunday throughout the season, and don’t require any special advanced ticket purchase. Just show up hungry!
16. Experience The Big E
One of the most beloved fairs in the Northeast is The Big E, which takes place mid-September through early October. In fact, it’s the world’s only multi-state fair, so it’s definitely something to experience once in your life.
The Big E has all the fair favorites you can hope for including carnival rides, parades, live music and tons of vendors. This is the perfect way to say goodbye to summer, and hello to the fall season in New England.
17. Take A Haunted Tour
Massachusetts is home to some of the best spooky tours, haunted houses, and famous ghost sightings in the country, so doing some kind of spooky tour should be high on your list when visiting Massachusetts in the fall.
One of the most haunted places in the state that offers tours is the famous Lizzie Borden house in Fall River. You can even book an overnight stay here if you’re brave enough (spoiler alert, I am not 😂). Fall River is also home to the very scary Factory of Terror haunted house, so you can easily visit both for a full night of thrills.
And of course, Boston is home to some of the best haunted tours in the state! Here are a few of the best ones to look into:
→ Ghosts & Gravestones Haunted Trolley Tour
→ Haunted Ghosts & Pub Walking Tour
→ Death & Dying Night Walking Tour
Some super scary haunted houses to check out around Massachusetts are DementedFX, Fear Town, and 13th World Fright Park. But I actually have an entire post that rounds up the scariest haunted houses and places in Massachusetts, so be sure to check out that post at the end of this section.
18. Head To An Apple Orchard, Of Course!
It’s not fall in New England until you’ve visited an apple orchard, and there are tons of them all over Massachusetts that provide the quintessential fall experience!
If you’re visiting The Berkshires region, some great ones to check out are:
→ Hilltop Orchards
→ Bartlett’s Orchard
→ Meadowbrook Orchards
If you’re visiting the central and eastern parts of the state, these are some fun ones to visit:
→ Carlson Orchards
→ Red Apple Farm
→ Brookfield Orchards
19. Enjoy The Foliage Views From The Bridge Of Flowers
In the cute little town of Shelburne Falls in The Berkshires, the Bridge of Flowers is a famous attraction in the spring and summer. And while there isn’t as much in bloom in the fall season, it offers some pretty amazing views of the foliage-covered mountains right from the bridge. In fact, the entire town is another destination for a fun fall day trip or getaway.
And even in the fall, if you time your visit before a big frost, the bridge will still be blooming with some beautiful flowers, including dahlias, rudbeckia, daisies, and even some roses. October is the last month to enjoy blooms on this famous spot, so that’s just another reason to swing by in the fall.
20. Walk Through The Incredible Naumkeag Pumpkin Show
The gorgeous Naumkeag estate in Stockbridge puts on their Incredible Pumpkin Show in the fall season, and it’s most definitely worth checking it out!
Walk through the scenic grounds of the estate, glowing with festive fall displays and illuminated pumpkins. When you first arrive, you’ll see a food and beverage stand selling fun fall drinks (they had spiked apple cider, a fall mimosa, cider donuts, local beer, and non-alcoholic drinks when I was there – plus more!). I recommend grabbing something when you first arrive to enjoy during your walk. There is another beverage stand halfway through the way, too.
Since Stockbridge is such a charming town in The Berkshires, it’s easy to plan an afternoon enjoying Main Street, grab dinner at the famous Red Lion Inn before heading to Naumkeag for the perfect night of fall fun!
Pro Tip: The best time to get your tickets for the show, since it’s timed entry, is about 15-30 minutes before sunset. That way, you can enjoy part of the walk at sunset, and then the rest of it afterward, and enjoy the illuminated displays after dark.
21. Find Your Way Through A Corn Maze
Massachusetts has some pretty amazing corn mazes to check out, and since this is such a time-honored tradition in the fall season, this is one activity that should be on everyone’s radar.
One of the best to check out in the state is the Davis Mega Maze in Sterling. The maze itself is an experience on its own, and spans over 3 miles of trails to get through. It can take anywhere from 30 minutes if your sense of direction is on point, or up to 3 hours!
On top of that, the entire farm is the perfect fall destination, and you’ll find all kinds of activities in the fall season for their Davis Farm Festival including zip lines, awesome food, local beer, live music, and so much more.
Here are some of the best corn mazes in Massachusetts to check out this season:
→ Mike’s Maze
→ Flint Farm
→ Marini Farm Stand
→ Crescent Farms
22. Make Your Own Fall Candle In Rockport
One of the more unique things to do this fall is to make your own candle at Rockport Candle Company. Rockport is one of the most charming coastal towns in New England, and while it’s not a super popular fall destination, it’s special to visit year-round.
And Rockport Candle Company has a very fun DIY Candle Bar experience, where you’re guided through the process of creating your own custom scent, and pouring your own candle. Since so many of us just love a cozy night in with the perfect fall candle, this is one of the coolest things to do this fall.
23. Enjoy The Quiet Coastline
While most people flock to all the best foliage spots around the state in the fall, the Massachusetts shore garners the nickname “the quiet coastline.” Since the coast’s big season is the summer, it mellows out quite a bit after mid-September, and this is a wonderful time to experience the most beautiful parts of the waterfront.
Places like Cape Cod and the Islands are wonderful this time of the year, and you’ll be able to find deals on hotels, and far fewer crowds. While the water will likely be too chilly for a swim, the beaches and coastline are just as beautiful in the fall season as they are in the summer.
For that reason, booking a coastal Massachusetts stay in the fall is a great way to celebrate the season! Order some comforting clam chowder, take a brisk stroll on the beach, enjoy sales at the shops, and hit up the gorgeous nature trails!
24. Tour A Cranberry Bog
Also on Cape Cod, one of the most iconic fall events is cranberry harvest season, and if you time your visit just right, you can watch a cranberry bog harvest.
Cranberry harvest season in this area is late-September through November, and there are a few places that offer bog tours in the fall, including a cranberry farm in Harwich (one of my favorite Cape Cod towns!), and Cape Cod Cranberry Bog Tours in Orleans.
You don’t have to be on Cape Cod to tour a bog, though, and you can also check out A.D. Makepeace Company in Wareham, and Stone Bridge Farm in Acushnet.
25. Take A Scenic Fall Walk Or Hike
Between mountain peaks in The Berkshires, and cool waterfalls to check out, there are so many great hikes in Massachusetts with awesome fall color.
As mentioned earlier, Mount Greylock in The Berkshires is an epic hike if you’re up for climbing the state’s highest peak! The fall color at the summit is truly amazing this time of the year.
But if you’re looking for more, here are some other great hikes to take in the fall:
→ Wachusett Mountain State Reservation
→ The famous Walden Pond for a relaxing nature walk
→ Great Blue Hill (perfect for those near Boston)
→ The Cascades Trail in The Berkshires
→ Mount Tom State Reservation
→ Monument Mountain Reservation
→ Bish Bash Falls (the tallest in Massachusetts)
And as mentioned, the Sheep Hill and Field Farm walks in The Berkshires are wonderful during foliage season!
26. Sample All The Pumpkin Brews
Massachusetts is home to some of my all-time favorite breweries, and the fall season is especially wonderful to visit because you can taste what they’re brewing with all the flavors of this cozy season.
My No. 1 favorite brewery in Massachusetts that I just love to visit is Treehouse Brewing, which has locations in Sandwich on Cape Cod, Charlton, and Deerfield. During this time of the year, they’ll often release their “Autumn” Double IPA, which is just 👌🏻
Some other great breweries in Massachusetts to check out this fall are:
→ Trillium Brewing in Boston
→ Brick and Feather Brewery in Turners Falls
→ Greater Good Imperial Brewing Company in Worcester
→ Berkshire Brewing Company in South Deerfield
→ Jack’s Abby Craft Lagers in Framingham
27. Try The Hard Cider, Too!
I do love a good fall beer, but I’ve recently become more of a hard cider person, especially in the fall season. Massachusetts has some of the coolest cideries in New England to check out.
One of my all-time favorites is Far From The Tree in Salem, MA (perfect place to stop if you’re visiting this fall!). I’m so in love with their Bog cider, which has notes of cranberry, sage, and thyme. It’s honestly just fall in a can, and they only release it in the autumn months.
Some other great cideries in Massachusetts to visit this fall are:
→ Hilltop Orchards in The Berkshires
→ West County Cider in Shelburne Falls
→ Carr’s Ciderhouse – an awesome little hidden gem!
→ Ragged Hill Cider Company in West Brookfield
→ Common Ground Ciderworks in North Brookfield
→ Downeast Cider House in East Boston
28. Watch The Head of the Charles Regatta
One of the most famous events that takes place in the fall season in the Greater Boston region is the Head of the Charles Regatta in Cambridge. Even if you’re not super into rowing, this is still a really fun event to witness because the scenery is beautiful, and anyone can have an appreciation for how tough this sport is. I’m not much of a sports person, but it’s still pretty fun to cheer these guys on!
This event takes place in October each year over the course of 2 days, and it almost always coincides with peak foliage in the area.
29. Squeeze In Your Last Whale Watch Of The Year
October in New England brings the end of whale watching season, and this is the time to squeeze one in before the whales migrate too far south for the rest of the season. And Massachusetts is the best state for whale watching in New England!
Most tours in Massachusetts head out to the Stellwagen Bank National Marine Sanctuary, which is a world-renowned whale watching destination. Some great tours to check out before the end of October are:
→ Gloucester Whale Watch
→ Boston Whale Watch
→ Dolphin Fleet Whale Watch From Provincetown
→ Newburyport Whale Watch
30. Get Coastal At An Oyster Or Chowder Fest
While the Quiet Coast is a great place for a fall trip for so many reason, I’m going to throw one more out there to further entice you: Seafood Fests!
There are so really awesome seafood fests that take place along the coast this time of the year, and while it’s not necessarily the most “fall” thing to do, it’s definitely a very New England thing to do that often coincides with beautiful, fall weather. And if you love good seafood, this is something you’ll want to have on your radar.
Wellfleet on Cape Cod hosts its annual OysterFest every October, and you’ll find raw bars, craft vendors, and more delicious food during this very fun event. Plus, you’re on Cape Cod – what more could you want? 😉
Newburyport also hosts a wonderful seafood event called Oysterfest in the Port, typically taking place at the end of September each year. During the event, you can sip on local beer and wine, local oysters (of course!), and enjoy live music, and tons more delicious food.
Lastly, be sure to check out the Seaport Chowderfest in New Bedford! Usually taking place in early October, you’ll be able to sample tons of amazing chowders from all over the state, and you can vote on your favorites!
Here are some posts on the destinations mentioned above to help you plan:
- Boston In The Fall: The Best Things To Do!
- Best Things To Do In Newburyport, MA
- The Ultimate Salem, MA Day Trip Guide + Best Things To Do
- The Best Haunted Houses & Spooky Tours In Massachusetts
- Best Things To Do In Rockport, MA
Fun Fall Festivals In Massachusetts
31. Berkshire Botanical Gardens Harvest Festival
If you’re spending any time in The Berkshires this fall, you’ll want to plan a visit to the Berkshire Botanical Gardens Harvest Festival. Featuring over 100 artisan and food vendors, there’s so much fun to be had here. They go all out with fall-themed fun, and offer a haunted house, a hay maze, cider pressing, and and endless list of children’s entertainment like face painting and more.
During the event, you can also shop at their farmer’s market, pick up some plants, and enjoy the tag sale!
32. AppleFest At Cook’s Farm In Brimfield
This super fun family festival in Brimfield takes a perfect day of apple picking up a notch. In addition to PYO apples during the festival, you can also enjoy free wagon rides, pumpkin painting, live music, great food, and lots of activities for the kids.
This festival typically takes place at the end of September each year, and they do a great job advertising the dates and activities on their Facebook page.
33. Johnny Appleseed Arts & Culture Festival In Leominster
As of writing this post, the Johnny Appleseed Arts & Cultural Festivals has been a Leominster tradition for 30 years! This festival is completely free, and there are over 200 vendors to enjoy. They also claim to have the “world’s best apple crisp.” Not sure if you agree? Guess you’ll have to check it out for yourself to find out!
You’ll also find lots of activities for the kids at this event, and live music to enjoy while you dig into all the amazing food available.
34. Oktoberfest In Douglas
This fall street fair is one of the best in the state to check out, and many of the proceeds from the event go to local charities, so you can feel extra good about participating.
Vendors line the downtown streets with delicious food, unique crafts, and fun games. Kids will love the giant slide and obstacle course, and adults will have a blast in the prize cash cube. And of course, you can expect fan favorites like live music, and a cool atmosphere.
35. Thanksgiving In Plymouth
Last but not least, a great way to celebrate the end of the fall season is by visiting Plymouth for all their fun Thanksgiving festivities. As the site of the original Thanksgiving feast, the town goes all out throughout the month of November to celebrate the holiday.
There’s a parade the Saturday before Thanksgiving, special concerts, a waterfront festival, harvest market, and of course, an authentic Thanksgiving dinner held at the Plimoth Patuxet Museum. This special dining event serves a full Thanksgiving dinner, and includes actors portraying Pilgrims, so this is the ultimate way to experience the holiday.
Psst! I have an entire post on things to do that make Plymouth, MA worth visiting, if you’d like more ideas for your visit 😉
Best Places To Stay In Massachusetts In The Fall Season
Planning a fall getaway in Massachusetts and not sure where to stay? Here are my suggestions:
Boston: A great home base, especially if you’ve never been. It’s easy to take day trips from Boston to places like Salem, Newburyport and Ipswich, and it has the biggest International airport for the cheapest flight options.
Where To Stay In Boston:
🍁 Boston Harbor Hotel: Perfect, 5-star hotel on the waterfront.
🍁 The Revere Boston Common: Amazing location walkable to most of the top foliage sites in the city.
The Berkshires: Obviously, this is an amazing region to stay in the fall season in Massachusetts! And there are so many wonderful towns to pick from, so you can really tailor it to your preferences. I personally love Williamstown, Stockbridge and Lenox. You can also easily take day trips to places like Deerfield and Sturbridge from The Berkshires.
Where To Stay In The Berkshires:
🍁 The Williams Inn in Williamstown: Incredible inn with cozy, but modern rooms, and an upscale feel.
🍁 The Red Lion Inn in Stockbridge: Historic inn with cozy rooms and a great location on Main Street.
🍁 The Brook Farm Inn in Lenox: Charming inn with a traditional New England style and a great location.
Newburyport: If you’re looking to explore Boston & Salem on your fall trip, but want to stay in a place that’s less crowded and more like a small town, Newburyport is perfect. As mentioned, it’s a short drive from Salem for an easy day trip, and you can easily explore Ipswich, and Cider Hill Farm from here. And since you’re on the North Shore, you can make this a fall/coastal getaway by also seeing Rockport and more towns along the coast.
Since Newburyport is almost to the New Hampshire border, it will be easy to take some day trip there as well, including the charming city of Portsmouth!
Where To Stay In Newburyport:
🍁 Compass Rose Inn: A very cozy, traditional New England style inn where every room in a suite, and you always get an incredible breakfast each morning.
🍁Essex Street Inn: A more budget-friendly option that’s still an awesome location, and very quaint and cozy!
You may also find these posts helpful:
- The PERFECT New England Fall Road Trip Itinerary
- Fall In New England: The Absolute Best Things To Do & See!
- Things To Do On Cape Cod In The Fall
- Is New England In November Worth Visiting?
- Thanksgiving In New England: Cozy Getaway Ideas & Things To Do!
- Best Stops To Make When Driving From Boston To New York City
That’s A Wrap On Celebrating Fall In Massachusetts
And there you have it! All my tips and suggestions on the best ways to enjoy fall in Massachusetts. In fact, with so many fun and festive things to do, it’ll be hard to squeeze it all in before the snow begins to fall. But one thing’s for sure – every moment of autumn in the Bay State is simply glorious.
