Bash Bish Falls in Massachusetts.

12 Top Places To Visit In Massachusetts This Fall

There are plenty of reasons why fall is such a great time to travel. First off, the gradual drop in temperatures makes the outdoors conducive for exploration. Plus there’s just enchanting scenery at every turn and plenty of events going on everywhere so the atmosphere is far from boring even with the departure of many summer tourists. With that said Massachusetts is one of the top New England destinations to bask in the glory of autumn and experience fascinating moments outdoors. Starting from late September through October and November, this state’s regions, from the Berkshires to Central Massachusetts, dramatically blow up into mesmerizing scenes of vibrant foliage colors. This fall, witness the most incredible sights and enjoy exciting activities in the Bay State at these 12 top places, ranging from farms to scenic byways.

Bash Bish Falls

Bash Bish Falls in Massachusetts.
Bash Bish Falls in Massachusetts.

Massachusetts is home to many waterfalls where visitors can not only relish the views of these cascading natural beauties but also admire the colorful foliage surrounding them. Bash Bish Falls is one such fall, but it is unique as it is the highest single-drop waterfall in the state, making it a premier destination to visit in the fall. The waterfall comprises of cascades totaling 200 feet, while the final cascade drops from a height of 60 feet amid rocks. This waterfall is in the Taconic Mountains, and once here, visitors will be hypnotized by the dazzling beauty of the foliage around the waters. The views deserve a camera, and visitors are required to make only a 0.6-mile hike from the parking lot in Mount Washington town to enjoy the magic of falls here.

Berkshire Botanical Gardens Harvest Festival

Lake surrounded by vibrant fall colors in Massachusetts.
Lake surrounded by vibrant fall colors in Massachusetts.

Visiting the Berkshire region to bask in the beauty of autumn and take scenic drives or hike trails is incredibly rewarding. However, for those who want to party, have fun, and spend time socializing outdoors, the Berkshire Botanical Gardens Harvest Festival in Stockbridge is the place to be. Held in the second week of October, the festival is perfect for everyone, including families, as it features various activities such as cider pressing, hay rides, haunted house games, face painting, and other fall-themed activities. It also features a beer garden, a plant sale, an obstacle course, live music performances, and a farmer's market where guests can shop for various agricultural products. With over 100 food vendors and artisans, guests will also be spoilt with numerous choices of food, collectibles, plants, and souvenirs.

The Big E

Attendees of the Big E in West Springfield, Massachusetts.
Attendees of the Big E in West Springfield, Massachusetts. Editorial credit: Keith J Finks / Shutterstock.com

Fall is not just about foliage, apples, scenic drives, and leaf peeping. Festivals also make the season enjoyable and special, and The Big E is one of the biggest and most popular fall festivals in Massachusetts to check out. It is a premier agricultural fair involving all six New England states and the only multi-state fair in the United States. For those looking to enjoy an amazing fun time outdoors, the festival has it all. From parades, carnival rides, and a farmer's market to various tantalizing foods, agricultural exhibits, and musical performances, the event is a major fall highlight in the Bay State. Although dates may vary with each new year, the festival typically starts in mid-September and ends in the first or last week of October in West Springfield.

Connecticut River Byway

Sugarloaf Mountain overlooking Connecticut River in the fall at sunset.
Sugarloaf Mountain overlooks the Connecticut River in the fall at sunset.

The Connecticut River is the longest in New England with a byway running parallel to it. This byway runs for 39 miles in the Connecticut River Valley in Western Massachusetts and through several historic towns, including South Hadley, Hadley, Sunderland, and Northfield. While the byway offers unobstructed views of beautiful rolling hills, farmlands, floodplains, forests, and pastures year-round, the fiery colors of autumn add even more beauty to the natural features, making the entire ride all the more magical. Hit this byway this fall and be sure to stop at some top spots, including - Mount Toby Summit, the Hardley Farm Museum, and the Mount Holyoke Summit House.

Monument Mountain

An Asian woman standing atop a large rock on Monument Mountain in Great Barrington, Massachusetts.
An Asian woman standing atop a large rock on Monument Mountain in Great Barrington, Massachusetts.

Monument Mountain, one of the magnificent peaks in the Berkshires, is in the cozy town of Great Barrington. The mountain is a great stop in fall when its iconic summit at 1,642 feet offers spellbinding views of the Housatonic River Valley as it is carpeted with the enchanting orange, golden, yellow, and red shades of autumn. The Mohican Monument Trail (1.5 miles), Hickey Trail (0.83-mile), and Peeskawso Peak Trail lead to the summit, and on the way, hikers will encounter a large stone monument and plenty of rocks that serve as seats for picnics and the views.

Maudslay State Park

A dog swimming in a lake at Maudslay State Park, surrounded by lush greenery and tranquil water.
A dog swimming in a lake at Maudslay State Park. Editorial Credit: Kip Voytek via Flickr

Maudslay State Park is a recreational park along the Merrimack River in Newburyport, where visitors can experience the magic of fall before winter comes. As the foliage radiates its scarlet, orange, and yellow colors on the Merrimack River, it creates a picturesque natural scene that looks like an image on the cover of a travel magazine. Yet, there is more. The park is filled with meadows, landscaped gardens, towering pines, and mountain laurels, all glowing in the vibrant hues of autumn. Hike or bike the 16 miles of trails that wind through the forests, fields, historic stone bridges, and gardens to experience the mesmerizing scenery in the park. Otherwise, sit by the river banks to enjoy picnics with family and friends for a more relaxing experience.

Hilltop Orchards

View of Richmond Pond from Lenox Mountain in western Massachusetts.
View of Richmond Pond from Lenox Mountain in western Massachusetts.

Hilltop Orchards promises a super exciting fall experience for every visitor. This 100-year-old orchard offers a 4-mile loop trail where visitors can hike and enjoy sweeping views of the surrounding Berkshire hills. The vibrant fall foliage and panoramic vistas make it a perfect spot for nature lovers and photographers. Aside from hiking, visitors can pick apples from its 200-acre orchard featuring 27 apple varieties, enjoy hayrides, and taste freshly made cider donuts. The orchard also has a farm store where visitors can buy locally made goods, taste wine, and have a relaxing picnic with family.

Mount Greylock State Reservation

Autumn view in Mount Greylock State Reservation.
Autumn view in Mount Greylock State Reservation.

The Mount Greylock State Reservation Area is a unique destination worth a visit in October as it hosts Mount Greylock - the highest summit in Massachusetts at 3,491 feet. Views from here are panoramic and thrilling, especially in autumn. Fortunately, visitors can hike or drive to the summit to witness the magnificent color carnival of foliage carpeting the mountains and valleys. The 90-foot Veterans Memorial Tower is also on the summit, and from its observation tower, visitors can see several other mountain ranges soaked in colorful foliage. These include the Adirondack and Taconic mountains, as well as the states of New Hampshire and New York.

Quabbin Reservoir

Quabbin Reservoir in Massachusetts during peak foliage season.
Quabbin Reservoir in Massachusetts during peak foliage season.

Quabbin Reservoir is the largest inland water body in Massachusetts, and while its principal role is to supply water to Boston and other neighboring cities, it also does more. In fall, when the transforming leafage around it puts up a show, it becomes a hot spot to hike for the scenery. Plus, there are overlooks, notably the Observation Tower and Enfield Lookout, offering sweeping views of the scenery. Tourists can also launch a boat and explore the water as views of surrounding foliage and hills draped in red, orange, and yellow flora fill the eye. Keep in mind that recreational activities are regulated since the reservoir supplies drinking water to over 3 million people.

Walden Pond

Beautiful fall foliage at sunrise over Walden Pond in Concord, Massachusetts.
Beautiful fall foliage at sunrise over Walden Pond in Concord, Massachusetts.

Walden Pond is a beautiful small pond within the Walden Pond State Reservation Area in Concord that promises a captivating experience. Notably, the pond is popular in the state since it was the inspiration behind the critically acclaimed novel Walden, written by David Thoreau, who visited the pond and fell in love with it. As a result, it draws tourists year-round to its serenity, unsullied beauty, and still waters. In autumn, the natural colors of foliage around this breathtaking water body are almost indescribable. The best way to soak in this natural display of colors is to hike the short trails around the pond or sit by its small sandy banks to cherish them. Tourists can also swim or boat on the water while enjoying the views.

Mount Sugarloaf State Reservation

View of the Connecticut River and the Pioneer Valley looking east-southeast from Mount Sugarloaf in South Deerfield, Massachusetts
View of the Connecticut River and Pioneer Valley from Mount Sugarloaf in South Deerfield, MA. By Tom Walsh, CC BY-SA 2.5, Wikimedia Commons

The lookout tower on Mount Sugarloaf State Reservation Park offers otherworldly views of fall’s iconic foliage as it shines in shades of yellow, orange, red, and purple. These views are more spectacular as they surround the Connecticut River and Pioneer Valley, including typical New England farmlands, small rivers, and lush vegetation. Visitors can either hike the easier View of the Valley Trail or the challenging option - Pocumtuck Ridge Trail, for seasoned hikers. Alternatively, laid-back leaf peepers or hikers can drive up to the summit but with smaller vehicles, as the road leading to the top is a bit narrow. Meanwhile, the park is also a scenic destination where you can enjoy picnics alongside the foliage colors.

The Mohawk Trail

Aerial view of the scenic Mohawk Trail highway hairpin turn in autumn, Massachusetts.
Aerial view of the scenic Mohawk Trail highway hairpin turn in autumn, Massachusetts.

The Mohawk Trail is one of the most visually stunning drives in Massachusetts, lined with marveling landscapes of forests, mountains, and rivers. In fall, it becomes spellbinding as the colors of foliage enhance the already gorgeous scenery. This stunning drive is 69 miles long and goes through several towns, including Greenfield, Buckland, Clarksburg, and Williamstown. A significant portion of the trail even runs parallel to Deerfield River, and there are several overlooks along the route to stop and admire the foliage. Whitcomb Summit, the highest point on the route at 2,185 feet, is a must-stop as it is the best overlook to see the scintillating views within the valley and surrounding mountains. Other exciting stops along the route include Shelburne village and its bridge of flowers, the French King Bridge, and the Eastern Summit.

Experience Massachusetts’ Autumn Splendor

When autumn calls, the Bay State responds with some of the finest landscapes draped in scenic foliage colors, offering memorable adventures for the season. From hiking and leaf peeping to scenic drives and picking apples, there are plenty of things to do while soaking in the charming colors of foliage of this state. It is also a great time to partake in some popular festivals and fun family activities amid all the natural beauty. Keep in mind that the fall season peaks around mid-October in the state, so make arrangements to visit at the right time for the best views before the arrival of winter and its abundant snow.

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