Massachusetts Road Trip Ideas: 11 Best Road Trips + Itinerary

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!

As you decide which road trip to take first, check out OnlyInYourState’s Ultimate Road Trip Packing List for our best road trip planning and packing tips. Whether you’re leaving for a single day or a week-long road trip, you can’t forget the snacks: here are 50 on-the-go snack ideas perfect for traveling.

1-Day Road Trip In Massachusetts

Rockport, MA, USA

Maudib/ iStock / Getty Images Plus via Getty Images

• 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 road trip includes stops in Essex, Manchester-by-the-Sea, Gloucester, and Rockport. While just about an hour 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.

3-Day Weekend Road Trip In Massachusetts

Skinner State Park Road, Skinner State Park Rd, Massachusetts, USA

LN S / AllTrails

• 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

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.

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The Coastal Massachusetts Road Trip

Rockport, MA, USA

DenisTangneyJr/ E+ via Getty Images

• 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 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.

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The Massachusetts Central Hills Road Trip

Ware-Hardwick Covered Bridge, Ware, MA, USA

Dave Gilbert / Google

• 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

While you can do this 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.

Best Massachusetts Road Trip For Spring

Wahconah Falls State Park, 68 Wahconah Falls Rd, Dalton, MA 01226, USA

jpitha / Flickr

• 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 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.

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Best Summer Road Trip In Massachusetts

Marconi Beach, Wellfleet, MA 02667, USA

|vv@ldzen| / Flickr

• 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

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.

Best Massachusetts Road Trip For Fall

Brewster Gardens, 30 Water St, Plymouth, MA 02360, USA

masstravel / Flickr

• 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 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.

Best Winter Road Trip In Massachusetts

Lowell, MA, USA

masstravel / Flickr

• 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

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.

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Family Friendly Massachusetts Road Trip

Battleship Cove, Fall River, MA 02720, USA

Battleship Cove / Facebook

• 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 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

Old State House, 206 Washington St, Boston, MA 02109, USA

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• 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

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 route, 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.

Road Trip to Best Small Towns in Massachusetts

Newburyport, MA, USA

DenisTangneyJr / iStock / Getty Images Plus via Getty Images

• Route: Newburyport > Williamstown > Stockbridge > Hadley > Sturbridge > Eastham > Scituate > Marblehead > Rockport
• Distance: 584 Miles
• Trip Time: 11 hours driving time

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 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 Massachusetts road trips 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.