Sometimes we just need to get away, change our surroundings for a bit, and gain a different perspective on life. Even if it's just traveling within our own backyards, like on a Massachusetts road trip. If you've never explored Cape Ann, Massachusetts, we put together a short and sweet road trip to guide you. You'll see some incredible scenery and visit some of the best of what this rocky cape has to offer.
This short and sweet road trip in MA is just over 26 miles. You can follow the route and stop at several points of interest by using our interactive map. Let's get started!
Cape Ann is a rocky cape in the northeastern part of Massachusetts. It's comprised of the towns of Essex, Manchester-by-the-Sea, Gloucester, and Rockport along with Ipswich.
Start your journey in the town of Essex at Stavros Reservation. Part of The Trustees, this reservation sits atop a hill where you're guaranteed jaw-dropping views of both Crane Beach and the Essex River estuary.
After you take a short hike and enjoy the views, if you are looking for more fun things to do in MA, head into town for some shopping and dining along Main Street. Learn more about what you can do in Essex.
Next on this MA road trip, we head south to Manchester-by-the-Sea. The first stop here is the incredibly scenic Tucks Point where you can take in views of the harbor.
A stop at Manchester-by-the-Sea's Singing Beach is mandatory while you're in town. Walk along the sand and listen to the noises it makes under your feet. It's utterly fascinating!
We continue our road trip in MA to Gloucester where you can spend some time at the alluring Hammond Castle. Built in the 1920s, this castle once belonged to a prominent inventor.
Now a museum, you can take a self-guided tour and stroll its stunning grounds with water views.
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After Hammond Castle, hit the road and head into town where you'll see the Fishermen's Memorial. Gloucester is a busy port city filled with beautiful beaches, excellent seafood restaurants, and gorgeous scenery. Set aside enough time to explore all of these fun things to do in MA before heading off to Rockport.
The quaint town of Rockport is next on your MA road trip. While you're here, you may as well stop at Motif #1, one of the most photographed spots in Massachusetts.
Another point of interest in Rockport, albeit a quirky one, is the Paper House. Constructed (mostly) of paper, this house is one-of-a-kind and a must-see on your Massachusetts road trip.
As part of one of the best road trips in MA, a trip to Rockport would not be complete without stopping at Halibut Point State Park. Take a short, easy hike through the forest, by the quarry, and to the coast. It's so picturesque, you'll want to spend as much time here as possible.
Are you excited to take one of the best road trips in MA? Let us know about your favorite places on Cape Ann in the comments!
If you would like to extend this Massachusetts road trip a bit further, you can always head to Ipswich and stop by Castle Hill at the Crane Estate as well as Crane Beach.
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.
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.
