Start your journey in Plymouth, known as "America's Hometown." If you've never been, the Plimoth Patuxet Museum is a must-visit attraction, but the town's changed a lot since the Mayflower pilgrims washed ashore in 1620. Today, Plymouth is a thriving community teeming with great shops and food. Pop into a cafe like Kiskadee Coffee Co. for some espresso to fuel your travels.
If you hop in your car and head to your next stop, Sandwich, just 40 minutes away, your latte might still be warm when you arrive. Interested in continuing the historical theme? Visit the Hoxie House, one of Cape Cod's oldest structures, a saltbox building that's survived the waterfront weather since the 1600s. If you'd like a bite to eat, Sandwich contains some crave-worthy eateries. Local spots like Fishermen's View give diners a front-seat view of the busy harbor.
When you're ready to leave, buckle in for your drive to Provincetown, just over an hour away. I recommend budgeting time for impromptu exploration. U.S. Route 6 is famously beautiful, and you'll want to pull off to take in views and stretch your legs. Once you arrive, find something to eat and rest up for the night.
Rise bright and early, hunt down coffee, and head to nearby Chatham, a walkable Bay State gem. Here, you'll hitch a ride on the ferry and head across the sound to Nantucket.
No need to hurry. Nantucket deserves a day of its own, so you'll be spending the night. This idyllic community epitomizes the best of Cape Cod. From adorable shops to magical beaches, it's the perfect blend of breathtaking natural beauty and quaint small-town life. Is one day not enough time to see it all? Feel free to extend your stay.
Bid adieu to this tranquil island refuge the following morning, but not before striking out for a well-deserved latte. From here, you'll hop back on the ferry and return to the mainland.
Your next port for the night is adorable New Bedford. This drive closely hugs the shoreline, making it the ideal route for a beach picnic. Part of what I love about New Bedford is its historic atmosphere. Over the years, the button-sized community has done an excellent job preserving its older buildings. If you can, book a night in one of these historical homes.
Conclude your trip with a foray into the great outdoors at Freetown-Fall River State Forest. This gorgeous park contains 25 miles of trail, so come prepared with your hiking gear and a sense of adventure. Come to think of it, you might want some sage on hand, too. Rumor has it that these woods are haunted.
Stumped on where to vacation this summer? Check out this waterfront road trip in Massachusetts, built around the highlights of Cape Cod: its history and natural beauty.
We here in the commonwealth are so fortunate to have the gorgeous colors of autumn on full display right in our own backyards. There’s nothing like watching local flora flare with brilliant hues of gold and scarlet. The best way to see all the autumnal splendor? A fall foliage road trip, of course. Marvel at some of the best fall foliage in Massachusetts on this road trip that will take you all over the state.
The drive time for this road trip to some of the best fall foliage in Massachusetts is just shy of nine hours, so you may want to stop at the included overnight destination. For detailed driving directions, which you can easily customize to meet your timeframe and needs, check out Google Maps.
This family-owned farm has been providing an incredible bounty of fresh food and stunning fall colors in Massachusetts for nine generations of Appleton farmers. Roam the open pastures, golden fields, and beautiful orchards to get your fix of autumn beauty. The crimson ivy climbing across the farm’s rock walls is particularly stunning.
Located a mere six miles from Boston, Arnold Arboretum, a 265-acre leafy paradise, offers plenty of amazing spots for watching the leaves change colors in Massachusetts. Many of the trees are labeled, so you’ll know exactly what kind of colorful flora you’re looking at. The paths are well-marked and edged with brightly-hued leaves, and the arboretum is open daily from sunrise to sunset.
This park feels worlds away from the hustle and bustle of urban living, but it's located right in the Plymouth cultural district. Featuring carefully maintained walking paths and a babbling brook, this little park is a hidden treasure that is packed with gorgeous fall colors.
4. Where to Stay: Longfellow's Wayside Inn, Sudbury
This mill is the oldest operating inn in the country and the quintessential autumn hideaway. They've been welcoming guests since 1716, and grinding their own corn meal and wheat flour since 1929. This delicious flour is then used in their mouthwatering baked goods. Longfellow's Wayside Inn offers 10 guest rooms that are furnished with a combination of authentic antiques and period-inspired reproductions. It’s the perfect place to bed down for the night after a full day of foliage hunting.
This spot might be best known for its sublime skiing, but Wachusett Mountain transforms into a wonderland of fall colors around late September. Don't miss your chance to take in the beauty of this natural landmark without the winter crowds.
There’s something particularly special about Old Sturbridge Village in the fall. This open-air, living history museum recreates all the charm and stately beauty of colonial New England. There’s no better time to explore than during the autumn months when the village’s ancient trees are afire with dazzling shades of yellow, orange, and red.
Located right along the Mohawk Trail (one of the best routes for admiring the fall colors in Massachusetts), Deerfield is a charming town filled with wide lanes, colonial homes, and a profusion of brightly-colored autumn foliage. Stroll through the historic district and catch an eyeful of rich fall splendor.
8. Savoy Mountain State Forest and Florida State Forest
These two magnificent forests are right next to each other, so you can take your pick. Both offer incredible landscapes, especially during peak fall foliage. Florida State Forest is smaller and lesser known, so it might be the perfect spot to find a beautiful, shady grove all to yourself. However, Savoy Mountain State Forest has some of the most breathtaking views around.
This charming state park features a petting zoo and an ice cream shop, not to mention plenty of scenic walking paths and trails. The autumn season really brings out the beauty of Great Brook Farm State Park. For more information about the hiking trails in the park, check out AllTrails+.
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We can't go wrong with a road trip any time of year, but the autumn months are a particularly splendid time to hop in the car and go on a road trip to see the best fall foliage in Massachusetts. For another amazing trip across the state, check out our amazing waterfalls road trip through Massachusetts.
Where & When To See Fall Foliage In Massachusetts
Fall in Massachusetts promises plenty to do – picking pumpkins at our favorite pumpkin patch, escaping corn mazes, and going on hayrides. But the highlight of autumn for many of us is the breathtaking colors that paint the landscape in shades of gold, red, and orange. The leaf-peeping season in Massachusetts usually begins between the middle and end of September while the fall foliage typically peaks around the third week of October. Check out the week-by-week predictions for the fall foliage in Massachusetts this year.
Just as important as knowing when the foliage is expected to peak is deciding where to admire the autumn colors. While a stroll around the neighborhood or a trip to our local park often promises beautiful fall scenery, sometimes we want a little more. When adventure calls this autumn, answer with a visit to one of the more than 150 state parks in Massachusetts; breathe in crisp air on a fall hike, or roll down the windows for a drive along a meandering country road. All are prime leaf-peeping destinations in Massachusetts.
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Know Before You Go
Before you set off on this road trip to the best fall foliage in Massachusetts, confirm, if applicable, the destination’s hours and fees. Here are a few things to keep in mind:
Appleton Farms is open daily from sunrise to sunset. Members park free while non-members must pay a fee, which is slightly higher on the weekends.
Park at the Grist Mill for free at Brewster Gardens, which also offers free admission. The gardens are open from sunrise to sunset.
Wachusett Mountain State Park charges a parking fee of $5 for Massachusetts residents. Non-residents will pay a $25 daily fee. You can find free parking spaces in lots just outside of the park.
Old Sturbridge Village is open during select hours throughout the fall. If you purchase daily admission tickets online, you’ll pay slightly less than at the gate. Online rates are $27 for adults, guests 55 and older pay $25, ages four to 17 are $12, and children three and younger are free.
Open from sunrise to sunset, Great Brook Farm State Park charges a parking fee of $3 for residents of Massachusetts and $5 for non-residents.
One of the best parts of a road trip, besides the fall foliage? The food! After you visit Wachusett Mountain, fuel up with a delicious meal at The Barn in Princeton. The cozy restaurant, with large windows overlooking trees splashed with fall colors, features what it describes as a “seasonally-inspired” menu. Choose from a generous selection of appetizers, sandwiches, and entrees. The family-friendly restaurant also offers vegan and gluten-free options.
If you’ve got the time, why not extend your road trip by booking a stay at an enchanting Airbnb? Enjoy the quiet, about a half-hour from Deerfield, at a cozy country home in Wendell. Flanked by Wendell State Forest, the one-bedroom, one-bathroom Airbnb is brimming with amenities, including a private deck and a private backyard. Pets are allowed. Spend those chilly New England autumn evenings outside in front of the roaring fire pit, roasting marshmallows and gazing at the starry sky.
When most people imagine New England, they think of sandy beaches, seafood, fishing boats, and long roads to nowhere. Lighthouses and rocky coasts are certainly a part of the image, too. But, undoubtedly, of all the states in the region, there’s only one that offers every element of the quintessential New England. Massachusetts has it all! From winding roads to wide open beaches, hiking trails to roadside wonders. If you’re interested in seeing all of this, it might be time to consider a journey through the state. Here are a few of the best road trips in Massachusetts to get you started. Each one is fun, but all offer something uniquely different. Check them out the next time you’re adventure-ready!
Route: Stavros Reservation > Tucks Point > Singing Beach, Manchester-by-the-Sea > Hammond Castle, Gloucester > Fishermen's Memorial, Gloucester, Rockport > Paper House > Halibut Point State Park
Distance: 26 Miles
Trip Time: 1-hour driving time
If you’re looking for a road trip that brings you to all the quintessential beauty of New England, it’s certainly this one. Covering all of the Cape Ann area, this single-day road trip includes stops in Essex, Manchester-by-the-Sea, Gloucester, and Rockport. While just about an hour's drive, it’s best to set aside the entire day for the journey. There are quite a few stops you’ll want to take your time enjoying, including a great restaurant, a fun state park, and some historic sites you can’t miss. This day trip proves that Massachusetts is one of the best states in the USA for sightseeing in coastal towns, and quick road trips in Massachusetts can be an exciting adventure.
Route: Halibut Point State Park, Rockport > Skinner State Park, Amherst > Bash Bish Falls State Park, Mount Washington
Distance: 218 Miles
Trip Time: 4 hours driving time
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While we love the Massachusetts coast and the water, there’s something especially magical about the state parks that exist inland. Hiking trails, forests, and lots of opportunities for fresh air await throughout this Massachusetts road trip itinerary. You’ll begin in Rockport at Halibut Point State Park where you’ll find a lot to explore across 67 acres. And, if you happen to visit on a clear day, you might be able to spot New Hampshire's Isle of Shoals as well as Maine's Mount Agamenticus. Next, you’ll head to the 834-acre Skinner State Park in Amherst. Plan on bringing a picnic to enjoy at the scenic overlook. On day three make your way to Bash Bish Falls State Park in Mount Washington. This 424-acre state park sits on the Massachusetts border with New York and includes hiking trails and an epic waterfall. Weekend road trips in Massachusetts like this one give us the opportunity to explore each site more thoroughly.
Route: The Knob, Falmouth > Dexter Grist Mill, Sandwich > Plimoth Patuxet Museums, Plymouth > World's End, Hingham > Boston Tea Party Ships & Museum, Boston > Peabody Essex Museum, Salem > Rockport, Massachusetts
Distance: 141 Miles
Trip Time: 3.5 hours driving time
If there’s anything Massachusetts is known for it’s the coastal images of wide open beaches and adorable small towns. This coastal Massachusetts road trip exposes travelers to the best of this. Beginning in Cape Cod, travelers will make their way north from Falmouth heading toward Sandwich. From here the route hugs the coast making its way through the south shore into Plymouth. Check out some important American history here, including Plymouth Rock where the Mayflower landed. Ultimately you’ll be heading toward Boston and on to Cape Ann. History buffs will appreciate the museum in Salem for information on all things Witch Trials. Be sure to check out the antique shops in these towns, as well as the cafes, art galleries, and seaport.
Route: Bear's Den, New Salem > Quabbin Visitor Center, Belchertown > Ware River, Ware > Ware-Hardwick Covered Bridge, Ware > Swift River Reservation
Distance: 67 Miles
Trip Time: 1.5 hours driving time
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While you can do this Central Hills road trip any time of year, we especially love it during the winter when the landscape is covered in snow. The 56-mile route makes its way around the Quabbin Reservoir, visiting several small towns along the way. Taking this journey is a great way to see another side of Massachusetts if you’re used to spending time along the heavily-visited coast and Cape Cod. You can choose to begin in any of the towns along the way, but we recommend beginning in New Salem and making your way around the loop until you return. There are opportunities for hiking, river views, and even a chance to visit the state’s longest covered bridge. Built in 1886, this beauty is 37 feet long.
Route: Doane's Falls, Royalston > The Cascade, North Adams >Wahconah Falls, Windsor > Wahconah Falls, Dalton > March Cataract Falls, Williamstown > Bash Bish Falls, Mt Washington > Race Brook Falls, Sheffield > Umpachene Falls, New Marlborough > Campbell Falls, New Marlborough > Glendale Falls, Middlefield
Distance: 300 Miles
Trip Time: 8 hours driving time
Offering one of the most wonderful ways to experience the Berkshires, this waterfall road trip will bring you to some of the most beautiful waterfalls in the northeast if not all of America. This is another journey that can be taken year-round, but we love it in the spring when the water is rushing from recent snowmelt. The route is long, extending from the border of Vermont to the border of Connecticut. But, every dollar spent on gas is worth it for the views. You’ll want to plan on spending some time exploring the falls, so it’s best to try splitting this into two days.
Route: Bound Brook Island Rd, Wellfleet > Marconi Beach, Wellfleet > Cold Storage Beach, Dennis > Duxbury Beach, Duxbury > Rexhame Beach, Marshfield > Humarock Beach, Scituate > Half Moon Beach, Gloucester > Good Harbor Beach, Gloucester
Distance: 175 Miles
Trip Time: 4 hours driving time
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Head straight for Cape Cod to start this beautiful summer drive. While Provincetown isn’t a stop, it might be fun to spend a night there before making your way to Wellfleet to start the journey officially. Here there are two beaches that offer a great day in the sun. Once you’ve soaked up the rays, go onward to Dennis. Shallow water at this beach means warm temperatures. It’s also good for kids who are new to the beach. From here you’ll make your way to the heart of the south shore with stops in Duxbury, Marshfield, and Scituate. You might consider spending the night here to enjoy a local restaurant, a lobster roll, and ice cream. Next, you’re headed north to two gorgeous beaches in Gloucester. For those who have always dreamed of a New England summer, this road trip through Massachusetts should definitely be on your bucket list.
Route: Appleton Farms, South Hamilton > Arnold Arboretum of Harvard University, Boston > Brewster Gardens, Plymouth > Longfellow's Wayside Inn, Sudbury > Mount Wachusett, Princeton > Old Sturbridge Village, Sturbridge > Deerfield > Florida State Forest, Florida > Great Brook Farm State Park, Carlisle
Distance: 415 Miles
Trip Time: 9 hours driving time
Is there anything more delightful than being in New England during the fall? We say no and that’s why this fall colors road trip is a favorite. This getaway is perfect for early peak foliage all the way through the end of the season. It covers a lot of mileage which means you’re bound to see foliage in different phases, too. While tourists might head to places like Portland, Maine, or the White Mountains, we think this route offers all the views you need. Start in the northeastern part of the state, then head south before making your way into the center towards the Berkshires. This route even includes a recommendation for an overnight stay to turn this into a weekend jaunt. There are also sure to be rentals along the way and with a little advanced planning you could make this into a special vacation.
Route: Edaville Family Theme Park, Carver > Taunton Green, Taunton > National Shrine of Our Lady of La Salette, Attleboro > New England Botanic Garden at Tower Hill, Boylston > Forest Park, Springfield > Stockbridge, Massachusetts > Yankee Candle, South Deerfield > Lowell > Stone Zoo, Stoneham > Blue Cloud Gallery, Somerville
Distance: 376 Miles
Trip Time: 7 hours driving time
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The most wonderful time of the year is especially wonderful when you spend it in Massachusetts. There are so many ways to celebrate and one of the best is seeing the holiday lights throughout the state. This is a long road trip, so you’ll probably want to spread things out over the course of a weekend. Start the journey in the south shore at the Edaville Christmas Festival of Lights in South Carver. Then, you’ll make your way northwest before heading east ending near Boston.
Route: Berkshire Scenic Railway Museum - Lenox Station Museum, Lenox > The Eric Carle Museum of Picture Book Art, Amherst > The Amazing World of Dr. Seuss Museum, Springfield > Steaming Tender, Palmer > EcoTarium, Worcester > Old Sturbridge Village, Sturbridge > Battleship Cove, Fall River
Distance: 200 Miles
Trip Time: 4 hours driving time
Road trips are always fun, but finding one that’s entertaining enough for kids can be challenging. This is one of the best road trips to take in Massachusetts and it includes some fun museums and a themed restaurant, making it a great option for even the pickiest kids. You’ll start your journey at the Berkshire Scenic Railway Museum in Lenox. Enjoy a trip on a trolley by booking ahead, or simply explore the museum. From here you’ll head to Amherst for a trip to the Eric Carle Museum of Picture Book Art. This is a fun one for kids who enjoy books. The rest of the day is packed with other fun stops and even some snacks. In addition to the fun stops along the way, the route is also a beautiful one, including a scenic byway depending on how you choose to take the trip.
Road Trip to Massachusetts Landmarks & Natural Wonders
Route: Old State House, Boston >USS Constitution, Charlestown > Minute Man National Historic Park, Concord > Louisa May Alcott's Orchard House, Concord > Walden Pond, Concord > The House of the Seven Gables, Salem > Motif Number 1, Rockport
Distance: 781 Miles
Trip Time: 2 hours driving time
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Massachusetts is full of history, which means tons of iconic landmarks worth seeing. From college towns to monuments, you’ll find notable landmarks throughout the state. This historic attractions road trip, starting in Boston and heading north, offers a few of the best things to see if you love learning about the state’s history. Begin by checking out the Old State House in Boston. From there you’ll visit the world's oldest ship, the USS Constitution, which is part of the history museum in the Charlestown Naval Yard. After this, you’ll make your way to Concord for three fun spots, followed by a drive to Salem. Finally, you’ll end your trip in Rockport.
When people think of New England, they often imagine quaint, small towns with main streets and mom-and-pop shops. Massachusetts certainly delivers on this and that’s why this small town road trip is a local favorite. It’s long, so be sure you’ve got at least a weekend to do it. But, every mile is worth it. The destinations include coastal towns with history as well as classic beach towns. But, of course, the inland spots are also great. Begin in Newburyport with a visit to the maritime museum, then make your way all the way west to Williamstown. Eventually, the trip will take you back east to the south shore and Cape Cod. It’s a long journey, but a beautiful one worth taking.
Whether you make the journey from as close as Maine and New Hampshire or as far as New York or Canada, every mile spent on these road trips will be worth the gas. They showcase a different magnificent part of the state and are perfect for those who want to spend every day soaking up the beauty of the world around them. Have you been to any of the stops on these road trips? If you have any other Massachusetts road trip ideas, we’d love to read about them in the comments!
After tackling some of the best road trips in Massachusetts on this list, consider heading out for more. Sometimes a road trip doesn’t even need any particular destination. If you appreciate the beauty of a trip almost as much as the destination itself, check out The King’s Highway, America’s oldest road, which travels right through Massachusetts.
