Fall in Massachusetts is nothing short of magical. As summer fades, the air turns crisp, the trees blaze with color, and small towns come alive with harvest festivals, scenic drives, and the cozy comfort of autumn. From the misty peaks of the Berkshires to the cranberry bogs of Plymouth County, the Bay State offers one of the most varied and colorful fall foliage experiences in New England.
Helpful guides you might like:
- Ultimate Fall in New England Guide
- Guide to Salem for Halloween
- New England Fall Packing List
- New England Fall Foliage Prediction Map for 2025
- Ultimate One Week Fall Foliage Itinerary
- All New England Fall Guides here
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While nearby states like Vermont and New Hampshire often get the spotlight, Massachusetts deserves a place at the top of any fall traveler’s list. Whether you're in search of brilliant foliage, apple picking adventures, or a spooky Halloween vibe, you'll find it here—wrapped in shades of gold, amber, and fiery red. Cozy sweaters, cider donuts, and pumpkin patches? Yes, please.
In this guide, I’m sharing the best places to soak in the fall beauty across Massachusetts. Let’s dive into when to go, what to pack, and eight incredible destinations to experience the magic of autumn.
Table of contents
When Is the Best Time to See Fall Foliage in Massachusetts?
Fall foliage in Massachusetts typically peaks between early and mid-October, depending on the region. The Berkshires and higher elevation areas in the west see colors change first, often by late September or early October. Eastern and coastal regions, like Cape Ann and Boston’s North Shore, peak slightly later—around mid to late October.
For the best timing, plan your visit for the first three weeks of October. If you want to be extra precise, check a fall foliage prediction map to track when the leaves will be at their peak in each area.
What’s the Best Airport to Fly Into?
The easiest airport for most visitors is Boston Logan International Airport. From Boston, you can rent a car and reach nearly anywhere in the state in just a few hours. If you're heading straight to the Berkshires, Albany International Airport (NY) or Bradley International Airport (CT) might be closer options.
Having a car is a must for a fall foliage road trip in Massachusetts—you’ll want the flexibility to stop at scenic overlooks, explore country roads, and visit orchards and small towns along the way.
What Should I Pack for Fall in Massachusetts?
Massachusetts fall weather can vary a lot—mornings are crisp, afternoons warm, and evenings cool. The secret? Layers.
Bring:
- A warm jacket or fleece
- Comfortable walking shoes or hiking boots
- Gloves and a beanie (especially for higher elevations)
- A light raincoat or umbrella
- Reusable water bottle
- Sunscreen and sunglasses (yes, even in fall!)
- And of course: your camera or phone for all those gorgeous photos
Best Places for Fall in Massachusetts
1. Boston
While Boston is a bustling city year-round, it transforms into something truly special in the fall. Leaf-strewn cobblestone streets, historic architecture framed by golden maples, and cozy cafés on every corner make autumn in Boston picture-perfect.
One of the best places to enjoy the foliage is the Boston Public Garden and adjacent Boston Common. Stroll along the winding paths as the trees turn fiery red and orange, and be sure to take a swan boat ride or snap a photo at the iconic George Washington statue surrounded by autumn color.
The Beacon Hill neighborhood is especially charming in the fall—gas lamps flicker at dusk, and pumpkins decorate the stoops of historic brownstones. For even more color, walk along Commonwealth Avenue Mall, a tree-lined promenade that feels like an autumn runway.
Boston also boasts incredible fall day trips. Hop on the Harvard Bridge to explore Cambridge, where ivy-covered university buildings are aglow in fall hues. Or take a quick ferry to the Boston Harbor Islands for coastal foliage and scenic hikes.
Don’t forget to grab a hot cider from a local café, shop for cozy knits at Faneuil Hall Marketplace, or enjoy the seasonal menu at one of the city’s many award-winning restaurants. If you're visiting in October, Boston’s neighborhoods often host fall festivals, Oktoberfests, and Halloween events, especially in the North End and South End.
Boston combines vibrant urban energy with New England charm, making it the perfect starting point—or grand finale—for your Massachusetts fall foliage adventure.
2. The Berkshires
The Berkshires are Massachusetts’ crown jewel for fall. Rolling hills, mountain peaks, and peaceful forests burst into a kaleidoscope of colors—making this region the perfect place to take a scenic drive, hike, or simply relax and soak in the beauty.
Head to Mount Greylock, the highest point in the state, for sweeping views of fiery foliage. Drive up to the summit or take one of the many hiking trails. The views are unforgettable.
Charming towns like Stockbridge, Lenox, and Williamstown offer a picture-perfect New England backdrop—think white steeples, stone walls, and historic inns surrounded by blazing maples.
Don't miss the apple orchards here, either. Favorites include Hilltop Orchards (with hard cider tastings!) and Bartlett’s Orchard for warm cider donuts. It’s the perfect blend of natural beauty and autumn indulgence.
3. Mohawk Trail & Shelburne Falls
One of the best fall drives in the state is along the Mohawk Trail (Route 2), stretching across the northern Berkshires. This scenic byway winds through forested hills and over mountain passes, creating the ultimate leaf-peeping road trip.
Stop in Shelburne Falls, a small village known for the Bridge of Flowers, charming shops, and views of the Deerfield River. It’s a dreamy fall town that feels like a step back in time.
Make sure to pull off at the Hairpin Turn Overlook for panoramic valley views—and consider stopping at local roadside stands along the way for pumpkins, cider, and maple syrup.
4. Mount Wachusett & Central MA Orchards
Just an hour west of Boston, Mount Wachusett is a foliage hotspot in central Massachusetts. Drive to the summit or hop on the ski lift (open on fall weekends) for panoramic views stretching to the Boston skyline.
The surrounding area is also known for its apple orchards. Bolton Orchards and Red Apple Farm are fall favorites with apple picking, cider slushies, pumpkin patches, and plenty of photo ops.
If you're in the area in mid-October, don't miss AppleFest at Wachusett Mountain—complete with craft fairs, food trucks, and foliage-filled chairlift rides.
5. Cape Ann (Rockport, Gloucester & Essex)
Fall on the coast? Yes, please. Cape Ann, just north of Boston, combines coastal views with classic New England charm—and a surprising amount of fall color.
Stroll through Rockport and Gloucester, where seaside homes are framed by glowing maples. Visit Halibut Point State Park for sweeping ocean views, or explore antique shops and seafood shacks in Essex.
A must-stop is Russell Orchards in Ipswich—perfect for apple picking, cider donuts, and admiring the fall colors near Crane Beach.
Bonus? Crowds are smaller than in summer, making it the perfect peaceful coastal escape.
6. Plymouth County Cranberry Bogs
Fall in Massachusetts isn’t just about leaves—it’s also cranberry harvest season! From mid-September through early November, the bogs in Plymouth County transform into bright red pools as the berries are harvested.
Take a cranberry bog tour in Wareham or Carver, or simply drive the backroads and spot the crimson-colored fields from the road. It's a sight unlike any other.
Pair it with a visit to Plimoth Patuxet Museums or stroll historic downtown Plymouth with a cider in hand.
7. Salem
Known for its spooky history, Salem is the ultimate Halloween town. But come in October, and you’ll also find fall foliage lining the streets, seasonal events, and the town fully decked out in autumn decor.
Find my full guide to Salem here!
Explore the Witch House, take a ghost tour, or visit filming locations from Hocus Pocus. October weekends are packed with costumed visitors, food stalls, and spooky fun.
If Halloween is your thing, Salem in October is a must-visit. Just be sure to plan ahead—it gets busy fast.
8. Lexington & Concord
These historic towns just outside Boston are not only known for their Revolutionary War landmarks, but also for glorious fall foliage along leafy trails and colonial streets.
Walk through Minute Man National Historical Park, hike around Walden Pond, or visit the Old North Bridge surrounded by golden leaves.
It’s an easy day trip from Boston and a beautiful way to combine history with the season’s best colors. Don’t forget to stop for lunch at Concord’s Colonial Inn—especially if you want to dine with a view of the town green.
9. The Pioneer Valley
The Pioneer Valley in central-west Massachusetts, along the Connecticut River, offers pastoral beauty, charming towns, and rich history.
Drive the scenic backroads between Deerfield, Northampton, and Amherst, where rolling fields meet hills dotted with red barns and golden trees. Historic Deerfield is especially picturesque in autumn and full of colonial charm.
Visit Quabbin Reservoir for mirrored lake views surrounded by vibrant forests, or enjoy a cozy afternoon at a local orchard with hot cider and homemade pies.
Optional Add-Ons:
- Pick Your Own Apples at Tougas Family Farm in Northborough or Honeypot Hill in Stow
- Hike the Blue Hills Reservation for foliage views just outside Boston
- Drive the Scenic Route 112 through Huntington and Chester for lesser-known but stunning fall views
- Visit a Cider Mill like Carr’s Ciderhouse in Hadley for locally pressed cider and farmstand snacks
Massachusetts in the fall is truly something special. Whether you’re looking for a scenic mountain escape, a coastal weekend away, or a Halloween adventure, there’s something for everyone. And no matter where you go—from the highlands of the Berkshires to the red glow of the cranberry bogs—you’ll find yourself surrounded by the magic of autumn.
Pack your flannel, grab a cider donut, and hit the road. Fall in Massachusetts is waiting.
Read More:
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2025 Fall Prediction Foliage Guide
The Perfect New England Fall Road Trip
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Best Places for Fall in New Hampshire
Best Places for Fall in Connecticut
Ultimate One Week Fall Foliage Itinerary
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