1. Route 2 or Mohawk Trail
For an absolutely stunning drive through the colorful forests of Massachusetts, take a trip down Route 2 (also called Mohawk Trail). This historic road goes through the northern Berkshire Mountains, giving you plenty of opportunities to see dazzling sugar maples, white and red oaks, yellow birch trees, hemlock trees, and white pines. Many say that the best stretch is from Greenfield to North Adams (about 35 miles). Starting in Greenfield, you can check out the Rocky Mountain Park along the Connecticut River for hiking, biking, and bird-watching. Poet’s Seat Tower is a fun place to visit as well and provides excellent views of the surrounding fall foliage. Another great side trip along Route 2 is to take a visit to Shelburne Falls. This charming town is a little west of Greenfield, but it’s worth the extra trip. The beautiful Bridge of Flowers sits in the middle of the town, planted with over 500 different types of flowers, shrubs, and vines. One of the best spots for leaf peeping in Massachusetts is the hairpin turn along Route 2. The hairpin turn looks out across the Hoosac Valley, Mount Prospect, and Mount Greylock, and is 1,700 feet above sea level. Here you can witness an ocean of colorful trees, and it is also a beautiful spot to watch the sunset. The hairpin turn sits on the Clarksburg and North Adams town lines so that you can stop in at either town for dinner.
2. Mount Greylock
If you want to see the fall splendor from the highest vantage point in Massachusetts, head out to Mount Greylock. On clear days, you can stand on the peak and see over 90 miles of glorious foliage across the Taconic Range and the Green Mountains of Vermont. However, getting there is a bit of a hike, as the top is nearly 3,400 feet high, so plan on a few days of climbing. But if you’re up for an adventure, Mount Greylock cannot be beat. There is even food and a place to stay at Bascom Lodge when you reach the top of the mountain. While the peak offers glorious views of the surrounding landscape, you can also explore some of the shorter routes on and around the mountain. The nearby Lakeview Orchard in Lanesborough offers gorgeous views of Hoosac Lake. While you’re there, you can enjoy some fresh plums, apricots, and apples from the orchard.
3. Walden Pond State Reservation
History and picturesque fall scenery come together at Walden Pond State Reservation. Back in the 1800s, Ralph Waldo Emerson and Henry David Thoreau often escaped to Walden Pond to enjoy the tranquility and beauty of nature. Thoreau wrote an entire book about his time in the area (Walden; or, Life in the Woods), and it is easy to see why he loved it so much. Surrounded by hardwood trees with dazzling fall colors, the 62-acre Walden Pond is a serene and stunningly beautiful spot for leaf peeping in Massachusetts. Enjoy picnicking, hiking, swimming, and even fishing at Walden Pond. Keep your eyes open for chickadees and red-tailed hawks among the bright fall leaves. When the weather is warm, many people also enjoy wading into the water along the shore, or kayaking, canoeing, and paddling on the pond. You can also find a replica of Thoreau’s cabin in the Walden Pond State Reservation on Route 126 in Massachusetts, and a visitor’s center in Concord. There are many other historical landmark attractions to see in Concord if you have the time. Sleepy Hollow Cemetery (where many famous authors and historical figures are buried) offers a beautiful scene in the fall. You can also visit the Old North Bridge, where the first Revolutionary War battle happened, the Old Manse, and the battlegrounds at Minuteman National Historical Park.
4. Connecticut River Scenic Byway
Traveling north to south from Northfield to Springfield, the Connecticut River Scenic Byway is a beautiful 39-mile trek through the picturesque farmlands, pastures, forests, and rolling hills of the Connecticut River Valley in western Massachusetts. It begins in South Hadley, at the junction of MA 47 and MA 116, and continues to the border of Massachusetts and New Hampshire. The drive goes through several historic villages that were settled during colonial times, like Northfield, Hadley, South Hadley, and Sunderland. You can stop at the many museums and botanic gardens along the route as well or enjoy the fall colors while river rafting and kayaking along the water. When you get to Springfield, you can check out The Amazing World of Dr. Seuss Museum or the MGM Grand Casino. If you’re a maple fan, the North Hadley Sugar Shack in Hadley is an amazing place to stock up on honey, jams, pancake mixes, and other delicious maple products.
5. Cape Cod
Southeastern Massachusetts is one of the very last regions of the state to transform in the fall. While many visitors come here during the summer for beach vacations, the beauty of the Cape in the fall cannot be overlooked. Fall colors come to Cape Cod later than the rest of the state, with peak foliage often in mid to late October and trailing off even into November. As the leaves change color, the entire landscape transforms, shifting the blue and green marshes, bogs, farmlands, and beaches to fiery hues of red, orange, and yellow. These golden tones dazzle against the vibrant blue of the ocean, giving the region a stunning contrast of lively color. Cape Cod is definitely one of the best spots for leaf peeping in Massachusetts! Fall brings pleasant weather, a comfortable dip in the lake, and no parking fees, which is always a plus. Enjoy basking in the sun on the golden sand and long walks along the seashore in peace, as there are few visitors to the Cape during the fall. There is also kayaking, paddle-boarding, and biking on scenic byways and through mountain forests. The whale-watching season goes through October, so you could even book an ocean tour for the day! Take Route 6A, or “Old King’s Highway” for an incredibly scenic fall ride as you wind along the bay and many of the oldest villages in the United States. Another great option is the Heritage Museums and Gardens in Sandwich, full of dazzling colors during the fall. There are also several farmer’s markets to attend and nature trails to explore. If you have time, you can stay the night at one of the many B&Bs in Chatham and enjoy picturesque views of the water.
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