14 Must-See Places This Fall In Massachusetts

Hey there, fellow travel enthusiasts! Ready to embrace the magic of fall in Massachusetts? Trust me, you’re in for a treat! 🎃

Grab your flannel shirts and pumpkin spice lattes, as we explore the 14 must-see places that are simply breathtaking during the Massachusetts fall season.

13. The Berkshires

If you’re on the hunt for an autumn escape that’s straight out of a postcard, look no further than the Berkshires in Massachusetts! Let me tell you, this place turns into a breathtaking kaleidoscope of colors during the fall season, and it’s an experience you won’t want to miss!

First things first, let’s talk about those foliage views! The Berkshires become a painter’s dream with vibrant reds, oranges, and yellows sprinkled all over those rolling hills. It’s like Mother Nature herself took a palette and went wild! Seriously, every twist and turn on those winding roads offers a new jaw-dropping scene, so keep your camera ready at all times!

Oh, but wait! There’s more to the Berkshires than just pretty leaves (although they do steal the show). If you’re an outdoor enthusiast, this place has got you covered! Lace up your hiking boots and hit the trails because there’s nothing quite like crunching through a carpet of fallen leaves while being surrounded by the golden glow of the woods.

Feeling artsy? You’re in luck! The Berkshires are home to some seriously cool arts and culture spots. The MASS MoCA (Massachusetts Museum of Contemporary Art) is an absolute gem, hosting fascinating exhibitions that’ll get those creative juices flowing. And don’t miss the cute galleries in charming towns like Great Barrington and Lenox – the local artists here are top-notch!

The Berkshires are a haven for food lovers. From farm-to-table eateries serving up fresh, seasonal delights to cozy cafes where you can warm up with a pumpkin spice latte, your taste buds are in for a treat!

Now, let’s talk about the cherry on top – fall festivals! The Berkshires know how to celebrate the season in style. Look out for harvest festivals, craft fairs, and pumpkin patches where you can pick the perfect pumpkin for your front porch.

If you’re worried about where to stay, don’t be! The Berkshires have a plethora of charming inns, cozy cabins, and boutique hotels that will make you feel right at home. Plus, the locals are super friendly and always ready to share their favorite fall haunts.

12. Salem

Halloween vibes, anyone? Salem comes alive in the fall with its spooky history and bewitching atmosphere. 

Now, you can’t visit Salem in the fall without indulging in some witchy delights! 🧙‍♀️ Embrace the Halloween spirit and visit the Witch Museum to learn about the town’s spooky past. And if you’re feeling adventurous, take a haunted walking tour to hear spine-chilling tales that will send shivers down your spine!

There are honestly SO many things to do in Salem in October. You could easily spend the whole month here!

Salem transforms into a picturesque wonderland with its streets lined with trees dressed in vivid shades of red, orange, and yellow. It’s like stepping into a real-life painting! Take a stroll through the town and soak in the enchanting colors – it’s an experience you won’t forget.

Feeling peckish after all that sightseeing? Salem’s got you covered! You’ll find a variety of cozy cafes and restaurants serving up delicious fall treats. From hearty pumpkin soups to apple cider donuts, your taste buds are in for a real treat!

And let’s not forget the fall festivities! Salem knows how to celebrate the season in style. Look out for pumpkin festivals, spooky parades, and other seasonal events that will make your visit even more memorable.

11. Cape Cod

If you’re dreaming of a coastal escape with a touch of fall magic, look no further than Cape Cod, Massachusetts! The summer crowds have dwindled, making it a perfect time to explore the serene beaches, lighthouses, and quaint coastal towns.

Cape Cod’s beaches and dunes take on a whole new charm with the leaves turning shades of red, orange, and gold. It’s a photographer’s dream come true! Take a leisurely stroll along the shore and breathe in that crisp fall air – pure bliss!

And guess what? The seafood here is still as fresh and delicious as ever! Treat yourself to a traditional New England clam chowder or savor some locally caught fish at one of the cozy seafood shacks.

Oh, and let’s not forget the cranberries! Cape Cod is famous for its cranberry bogs, and fall is harvest season. Take a tour of a cranberry farm and learn all about this tangy fruit – it’s an authentic Cape Cod experience you won’t want to miss.

Lastly, fall festivals! Cape Cod knows how to celebrate the season. Look out for harvest festivals, craft fairs, and even oyster festivals that will add a touch of festivity to your trip.

While you might not think of Cape Cod when you picture fall in Massachusetts, it’s actually one of the coolest (and least crowded) places to visit!

10. Mohawk Trail

Looking for quintessentially Massachusetts fall spots? This is one of the best for foliage.

This scenic highway takes you through the heart of autumn. The foliage along the route will leave you breathless – don’t forget your camera!

The Mohawk Trail takes you on a breathtaking journey through the stunning New England landscape, where every twist and turn offers a new burst of colors. It’s like driving through a living kaleidoscope!

This scenic highway is a must-see for all nature lovers. The rolling hills, picturesque forests, and charming small towns along the way will steal your heart. You can stop at various overlooks to take in the panoramic views or venture onto one of the many hiking trails for an up-close encounter with Mother Nature’s fall artistry.

What’s great about the Mohawk Trail is that it’s not just about the destination – the journey itself is an adventure! You’ll pass through quaint villages, historic sites, and even some roadside attractions that add to the fun of the trip. Don’t be shy to make spontaneous pit stops – you never know what hidden gem you might discover!

The best part? You don’t need to be a seasoned hiker or a nature expert to enjoy the Mohawk Trail. It’s accessible to everyone, whether you want to take a leisurely drive or opt for a short walk in the woods. Fall is the perfect season to explore this scenic route, as the weather is just right for outdoor activities.

As you venture along the trail, you’ll find plenty of charming places to refuel and recharge. From cozy cafes serving up pumpkin-flavored treats to family-owned diners with hearty meals, you won’t go hungry on this journey.

This is some of the best fall foliage in Massachusetts and isn’t to be missed!

9. Boston Common

The iconic park transforms into a wonderland of autumn hues. Grab a hot cider, sit on a bench, and watch the leaves fall – it’s truly beautiful!

As you meander through the park, you’ll come across various ponds, statues, and historic sites. Take a moment to admire the beauty of the Soldiers and Sailors Monument or have a leisurely paddleboat ride on the tranquil waters of the Public Garden nearby.

Fall is also a great time for people-watching in Boston Common! The locals are out and about, enjoying the cool weather and soaking in the fall ambiance. You might even spot some talented street performers adding to the lively atmosphere.

Oh, and let’s not forget the events! Boston Common hosts various fall festivals and gatherings, making it a hub of excitement during the season. Keep an eye out for outdoor concerts, food fests, and family-friendly activities that add to the festive vibes.

Boston Common is truly quintessential Massachusetts in fall and isn’t to be missed! There are so many great things to do in Boston in fall – this is only the starting place.

8. Monument Mountain

If you’re on the lookout for a breathtaking fall hike with stunning views, look no further than Monument Mountain in Massachusetts! This hidden gem offers a fantastic autumn adventure that will leave you in awe of the season’s beauty.

As you make your way up the trail, you’ll be rewarded with sweeping views of the surrounding valleys and hills dressed in their autumn best. It’s the perfect opportunity to take some stunning photos and capture the magic of fall.

Once you reach the summit, you’ll be treated to a panorama that’s simply breathtaking. Take a moment to sit back, relax, and soak in the beauty of the landscape. The foliage is some of the most stunning in all of New England!

Monument Mountain also has a rich history, adding an extra layer of intrigue to your hike. It was famously explored by literary figures like Herman Melville and Nathaniel Hawthorne, who found inspiration in its natural beauty. You can even find a plaque dedicated to Melville at the summit.

This is some of the best fall foliage in Massachusetts and is a great spot for the whole family.

7. Newburyport

Looking for a charming fall destination that’s a perfect blend of coastal beauty and autumn vibes? Say hello to Newburyport, Massachusetts!

First things first, let’s talk about the star of the show – the fall foliage! Newburyport’s streets and parks are lined with trees that burst into shades of red, orange, and gold during the fall season. You’ll feel a bit like you’ve walked into Stars Hollow.

Newburyport has that quintessential New England charm that you’ll fall in love with! The historic architecture, cobblestone streets, and quaint shops make for a picture-perfect setting. And don’t forget to explore the waterfront – the views of the Merrimack River with the fall foliage as a backdrop are simply stunning.

Now, if you’re a foodie, you’re in for a treat! Newburyport’s dining scene is a delightful mix of coastal cuisine and seasonal flavors. From seafood shacks serving up freshly caught fish to cozy cafes offering pumpkin-spiced everything, your taste buds are in for a delicious adventure.

The town’s proximity to the water means there are plenty of opportunities for outdoor fun! Take a boat tour, go for a scenic walk along the waterfront, or simply sit back and enjoy the sea breeze. The fall weather adds an extra touch of magic to these experiences.

Fall festivals are a big deal in Newburyport! The town hosts various events and celebrations throughout the season, including harvest festivals, craft fairs, and more. It’s the perfect opportunity to mingle with the locals and experience the town’s friendly and welcoming spirit.

If you’re looking for small towns to visit this fall in Massachusetts, then I can’t recommend Newburyport enough! Plus, this is some of the best fall foliage in Massachusetts that isn’t in the middle of nowhere.

Looking for more details? Check out our favorite things to do in Newburyport here.

6. Maudsley State Park

Speaking of Newburyport, you won’t want to miss Maudsley State Park in Massachusetts! This hidden gem offers a stunning natural backdrop that’s perfect for embracing the beauty of autumn.

The park’s peaceful atmosphere and serene riverside views make it an ideal spot for relaxation and reflection. Take a break from the hustle and bustle of everyday life, and immerse yourself in the tranquility of nature. And of course, the gorgeous foliage!!

Maudsley State Park is a hidden treasure for photographers too! With its stunning foliage and picturesque landscapes, you’ll find plenty of photo-worthy spots to capture the essence of fall.

The park’s historic Moseley family estate adds an extra layer of charm to your visit. Take a stroll through the beautifully manicured gardens and explore the estate’s history. It’s a fascinating blend of nature and heritage that sets this park apart from the rest.

Fall is also a great time for birdwatching at Maudsley State Park. The park is home to a diverse range of bird species, making it a haven for bird enthusiasts. Don’t forget to bring your binoculars!

After your time at the park, you can explore the nearby towns and enjoy some delicious fall treats. From farm stands offering fresh produce to cozy cafes serving pumpkin-spiced delights, there’s something to satisfy every craving.

5. The Bridge of Flowers

The Bridge of Flowers, located in the charming town of Shelburne Falls, bursts into a kaleidoscope of colors during the fall season.

The best part? The Bridge of Flowers features a diverse array of flowers and plants, which means you’ll be treated to a variety of autumn blooms this fall in Massachusetts. From vibrant chrysanthemums to delicate asters, there’s no shortage of beauty to admire.

This transformed former trolley bridge showcases a different kind of artistry during the fall. The carefully curated collection of flowers, combined with the surrounding fall foliage, creates a stunning natural tapestry that will leave you in awe.

The Bridge of Flowers is also a perfect spot for photography enthusiasts. Capture the beauty of the bridge and the surrounding landscape as you meander along its length. The picturesque Deerfield River flowing underneath adds an extra touch of charm to your photos.

Plus, the town of Shelburne Falls itself is a delightful place to explore. Wander through its quaint streets, browse local shops, and treat yourself to some delicious fall treats at the nearby cafes and bakeries.

4. Old Sturbridge Village

If you’re looking for a unique and charming Massachusetts fall experience that combines the beauty of the season with a journey back in time, look no further than Old Sturbridge Village!

Old Sturbridge Village is a picturesque setting with its historic buildings, dirt roads, and horse-drawn carriages, all adorned with vibrant fall colors. It’s like stepping into a time capsule!

As you wander through the village, you’ll witness demonstrations of traditional crafts and skills, like blacksmithing, weaving, and hearth cooking. It’s a fascinating way to learn about the past and experience firsthand how people lived during the 1800s.

The fall festivities at Old Sturbridge Village are a treat for visitors of all ages. You can take part in apple cider making, corn husking, and other seasonal activities that add to the festive atmosphere.

Fall is also the season for special events and themed weekends at Old Sturbridge Village. Look out for events like Harvest Weekend, where you can learn about traditional New England harvest practices or Sleepy Hollow Experience, a theatrical performance based on Washington Irving’s classic tale.

The village’s historic tavern is a must-visit spot. Step inside for a taste of 19th-century hospitality and enjoy a hearty meal featuring seasonal dishes and traditional fare.

3. Fruit Orchards

It’s apple-picking season, folks! Head to one of the many orchards across the state to pick your own apples, enjoy fresh cider, and maybe even some cider donuts – yum!

Massachusetts is home to some fantastic orchards, and fall is the perfect time to grab a basket and get plucking. Whether you’re looking for sweet, crisp apples for snacking or tart ones for baking, you’ll find a wide variety to choose from.

And speaking of baking, you can’t go apple picking without enjoying some homemade apple pies or apple crisp! Many orchards offer freshly baked goods made from the fruits you pick – talk about a farm-to-table experience!

Pumpkin picking is another highlight of the season. Head to the pumpkin patches and search for that perfect gourd to carve or use as a festive decoration for your home. Don’t forget to snap some Insta-worthy pics in the pumpkin patch while you’re at it!

Aside from the fruit and pumpkin picking, many orchards offer fun activities for the whole family. Enjoy hayrides, corn mazes, petting zoos, and more! It’s a fantastic way to spend a day outdoors and make memories with your loved ones.

The fall atmosphere at the orchards is something truly special. The air is crisp, the leaves are turning vibrant colors, and there’s a sense of excitement in the air. It’s the perfect setting to escape the hustle and bustle of daily life and immerse yourself in the beauty of the season.

Check out our favorite places to go apple picking in Massachusetts here!

2. Quabbin Reservoir

If you’re craving a serene and breathtaking fall escape, you’ve got to check out Quabbin Reservoir this fall in Massachusetts! This hidden gem is a true oasis of tranquility, and it becomes even more magical during the fall season.

Quabbin Reservoir is surrounded by lush forests that transform into a kaleidoscope of colors during autumn. It’s like stepping into a fairytale! The reservoir’s reflective waters add an extra layer of beauty to the landscape, making it a photographer’s dream.

The best way to experience the fall beauty at Quabbin Reservoir is to take a leisurely drive along the scenic routes. The winding roads will lead you through picturesque spots with breathtaking views of the reservoir and its surroundings

For nature enthusiasts, there are plenty of hiking trails that meander through the forests and offer captivating views of the fall foliage. Whether you’re up for a challenging hike or a leisurely walk, there’s a trail for every level of hiker.

Quabbin Reservoir is also a fantastic spot for birdwatching during the fall migration. As you explore the area, keep an eye out for wildlife – you might spot deer, foxes, or even the occasional black bear!

The fall weather at Quabbin Reservoir is typically crisp and refreshing, making it the perfect time for a peaceful picnic by the water. And this is some of the most beautiful fall foliage in Massachusetts!

1. Nashoba Valley Winery

If you’re looking for a delightful fall escape that combines stunning vineyard views and exquisite wines, Nashoba Valley Winery in Massachusetts is calling your name!

Let’s start with the star of the show – the winery itself! Nestled in the picturesque Nashoba Valley, this winery offers breathtaking views of the vineyards painted in fall colors. It’s like stepping into a postcard!

But of course, we can’t forget about the wine! Nashoba Valley Winery is renowned for its handcrafted wines made from locally grown fruits. From their luscious reds to their refreshing whites and unique fruit wines, there’s something to suit every palate. The wine-tasting experience is a must-do!

As if the vineyards weren’t enough, Nashoba Valley Winery also boasts apple orchards that are in full bloom during the fall season. It’s the perfect opportunity to go apple picking and savor the sweetness of freshly picked apples.

The winery grounds are the perfect spot for a leisurely picnic. Grab a bottle of your favorite wine, some artisanal cheeses, and relax under the shade of the trees as you enjoy the scenic surroundings. It’s the epitome of fall indulgence!

Nashoba Valley Winery also has a cozy restaurant that serves up delicious farm-to-table dishes. Whether you’re in the mood for a hearty lunch or a delectable dinner, the seasonal menu won’t disappoint

The winery hosts various events and festivals during the fall, making it an even more exciting destination. From wine and cheese tastings to live music events, there’s always something happening at Nashoba Valley Winery that adds to the festive vibes.