Road Tripping Through New England: Must-Visit Fall Spots

Best spots to see fall foliage in New England

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Can you imagine the symphony of colors while sipping hot apple cider? New England is like a painting in autumn, with trees bursting in glorious reds, oranges, and yellows. The mix of the crisp air, over-the-top foliage, and heavenly apple cider donuts make it compulsory to revisit every year.
Navigating through the orchards, the enticing smell of fresh apples filled the air. I wondered- could anything be more serene? As I sat by the lake, crunching leaves underfoot, a perfect pumpkin pie in hand, I realized... Fall in New England was an adventure in itself. This is where your palate dances with happiness, and your soul finds peace. So, who's ready for a delicious escapade?

🍁 New Hampshire 🍁

🔸Kancamagus Highway

Take a scenic drive through the White Mountain National Forest on the Kancamagus Highway, a 34.5-mile stretch of road with breathtaking views and picturesque stops. Starting in Lincoln and ascending through the forest, there are plenty of opportunities to pull over and enjoy the view. Don’t miss the C.L. Graham Overlook near the summit of Kancamagus Pass or a picnic at Sabbaday Falls in Conway, just a short walk from the trailhead. And make sure to head north to Bretton Woods on 302 for stunning views of Mount Washington. Experience the beauty of fall foliage on this drive-thru adventure, and stay at the Kancamagus Swift River Inn for an equally idyllic accommodation with its hiking trails.

🔸Lake Winnipesaukee Loop

Road trip around New Hampshire’s biggest lake (we’re talking 97 miles of premium New England sights) and take in the waterfront views and bright autumn foliage. Stop for lunch and a stroll in any of the quaint towns along the route, like Meredith, or even stop for some outdoor activities (boating, fishing, and hiking).


Visitors to Lincoln, New Hampshire, can witness the beautiful changing colors of the leaves around late September and early October. The area offers a variety of hiking and walking trails, making it easy for everyone to enjoy the vibrant scenery. For a truly breathtaking view of the changing foliage on the Osceola Mountains, head to the Pemigewasset Overlook.

New Hampshire must see fall spots


In Franconia, visitors can take an 80-passenger cable car up to the 4,080-foot summit of Cannon Mountain at the Cannon Mountain Aerial Tramway. The rolling mountains full of colorful leaves offer a stunning and unique view. Don’t miss a visit to Suga for more fall foliage viewing opportunities.

🔸Sugar Hill

Sugar Hill in New Hampshire is a great option if you’re looking for a fall getaway. Not only does it offer stunning views of autumn foliage, but there are plenty of activities to enjoy. Book a weekend stay at the Sugar Hill Inn, where you can go hiking, take a trip on the Cog Railway, ride the gondola up Wildcat Mountain, and visit the local Harman’s Cheese & Country Store.


Another charming destination in New Hampshire is Portsmouth, a city along the shoreline. The best time to see fall foliage in this area is mid-October, according to Take a stroll down Portsmouth’s Market Square and admire the changing colors of the trees.

Not to miss fall spots in New England in Vermont

🍁 Vermont 🍁

🔸Route 100

The scenery in Vermont during the fall season is reminiscent of a picturesque storybook setting. The charming Route 100, free from billboards, meanders through quaint villages, inviting you to savor cider donuts and visit country stores. Hiking to the summit of Mount Killington rewards you with breathtaking vistas, and a journey along the 11-mile Green Mountain Byway is a must. For a weekend getaway, consider Stowe or Mad River Valley, where you can delight in farm-to-table cuisine, craft beer, and even experience the beauty of autumn foliage on a zipline tour at Arbortrek Canopy Adventures or Stowe Mountain Resort (home to the second longest zipline tour in the US). Don’t miss out on a visit to Shires.

🔸Shires of Vermont Byway

The picturesque region of the Shires of Vermont is nestled in the state’s southwest corner and is traversed by the scenic route 7A. The route leads through seventeen delightful towns, including the historic and charming towns of Bennington and Manchester. In Bennington, visitors can ascend to the top of the towering 306-foot-tall monument erected in 1891 to honor the Battle of Bennington. The monument provides an unparalleled bird’s eye view of the surrounding landscape, making it a must-visit destination for travelers. Additionally, visitors can explore the quaint town of Montgomery, which boasts its unique charm and attractions.


Discover the most stunning autumn foliage views in northern Vermont’s small town of Montgomery. This picturesque location is also known as “Vermont’s Covered Bridge Capital,” making it the perfect spot to capture Instagram-worthy foliage and bridge snaps. With six covered bridges to explore, take a leisurely stroll while sipping a warm beverage. For outdoor enthusiasts, venture onto the 15 miles of trails preserved by the Hazen’s Notch Association. Whether you hike the full distance or just a portion, it’s the perfect way to experience Vermont’s natural beauty. Montgomery offers the best of fall with its foliage and covered bridges, making it a memorable autumn escape. The town’s geography resulted in numerous covered bridges, with six still standing as excellent photography spots. Each bridge is surrounded by a colorful leaves display, creating a muted rainbow hue. Stay at The Inn, a boutique hotel that resembles a quintessential Vermont mountain chalet, to complete your Montgomery experience.


When you hear “Woodstock,” vibrant foliage might not be the first thing that comes to mind. However, this Woodstock – located in a different state – is one of the best places to experience the beauty of changing leaves and has been dubbed the “quintessential New England village.” Visitors can expect to find classic American charm, colorful and lush foliage, and a charming town with plenty of shops and restaurants to explore. Take a hike through the woodlands of the Marsh-Billings-Rockefeller National Historical Park to witness the foliage up close. Afterward, indulge in some fresh local cheese from the Billings Farm & Museum to satisfy your appetite. Woodstock offers a stunning destination on a perfect day filled with scenic blue skies and vibrant fall leaves. The town boasts multiple walking paths and covered bridges that allow visitors to fully appreciate nature’s transformation. For a unique experience, visit the New England Falconry and hold a real falcon.


If you’re planning a trip to Vermont to witness the stunning autumn foliage, the best time to go is during the first week of October, as suggested by One of the must-visit destinations in the region is the picturesque mountain town of Stowe, which gained fame for its top-notch skiing facilities. However, even in the fall, the town is worth a visit to experience the breathtaking colors of the changing leaves. Visitors can explore the multicolored forest by hiking, mountain biking, or horseback riding. While in Stowe, the Stoweflake Mountain Resort & Spa is an excellent accommodation option, offering special fall packages and a comprehensive spa to help you unwind on chilly autumn days.

not to miss fall spots in massachusetts

🍁 Massachusetts 🍁

🔸Mohawk Trail

The Mohawk Trail, stretching over a mile, traces the path of a historical Native American trade route. It spans the Berkshire Mountains in northwest Massachusetts, encompassing the valleys of the Hudson and Connecticut Rivers. Along the way, you’ll find various mountain streams and rest stops. One such stop is the Golden Eagle restaurant, located at the trail’s famous Hairpin Turn, with an unbeatable view. The trail ends in North Adams, where you can visit MassMoCA, the Massachusetts Museum of Contemporary Art, one of the largest museums in the country. When it comes to viewing fall foliage in Massachusetts, the Mohawk Trail is a must-see destination. The 60-plus-mile road spans from the New York border to the Connecticut River and offers over 100 attractions to explore. You can drive, hike, or take a leisurely walk through the route. Don’t miss the Bridge of Flowers in the town of Shelburne Falls, an old trolley bridge that comes to life with vibrant orange, yellow, and red maple leaves during fall. While in Shelburne, make sure to book a stay at the pet-friendly bed-and-breakfast, Cavalier Cottage for the ultimate New England getaway.

🔸Route 6A

The beauty and charm of Cape Cod villages persist beyond summer, making them a fantastic fall destination for anyone looking for postcard-perfect towns along Route 6A. Begin just after the Sagamore Bridge and follow the road through scenic Sandwich, the Cape’s oldest town. Continue on to Yarmouth Port, through Dennis, and finally Brewster. You’ll find Nickerson State Park there, where the 22-mile Cape Cod Rail Trail offers many picturesque views on foot. The peak season arrives late here, making it an ideal destination for leaf-peeping in mid-October or even later.

Must visit fall spots in Massachusetts


If small towns or rural hikes don’t interest you, Boston offers easily accessible views from its bustling historic city. You can take a relaxing stroll through the trees in Boston Common and the Public Garden, or opt for a walk or bike ride along the Charles River Esplanade. For some outdoor exploration, head to the Arnold Arboretum at Harvard, an outdoor museum of trees and the oldest public arboretum in North America. If you have a car, consider driving to Walden Pond, where you can see Henry David Thoreau’s surprisingly tiny cabin and enjoy the beautiful fall foliage reflected in the pond. Once you’ve had your fill of sights, be sure to check out the city’s incredible cultural scene, dining options, and shopping opportunities. You won’t be disappointed!

If you want to experience the spectacular fall foliage, consider taking a break from the city and heading out into nature. However, Boston is a great option if you prefer a city getaway. The city boasts a peak foliage season throughout October, with the best colors appearing around Halloween. There’s no shortage of options for leaf peepers to witness the changing seasons, including Boston Common, Back Bay Fens, and tree-lined neighborhoods such as the North End and Beacon Hill. Additionally, there are plenty of hotels in the city to choose from, with the Four Seasons being a top-notch choice that often provides fall foliage packages to enhance your stay.


The small town of Sunderland, Massachusetts, becomes a kaleidoscope of red, orange, and yellow leaves when September and October come around. For a perfect fall drive, follow Route 116 and pass through the idyllic town of Sunderland to see rolling hills of fall foliage for miles. Grab some hot cider or cocoa to enjoy while you take in the views.

Halloween and fall spots in Massachusetts


Experience gorgeous views and a bit of history in Concord. Not only can you look at some truly gorgeous trees, but you can also visit the Minute Man National Park, where the first battle of the American Revolutionary War was fought. History and beautiful foliage, can it get better than this?

🔸Shelburne Falls

The quaint city of Shelburne Falls is a great option if you want to skip the super-touristy areas this upcoming autumn. Spend the day exploring the small bridges, restaurants, shops, and buildings that make up the small area.


Speaking of things to do in New England in October, is there a better Halloween destination than Salem, Massachusetts? Salem has become synonymous with Halloween celebrations and draws crowds from all over the country. This is likely due to its infamy as the site of the 1692 witch trials, but Salem is still a witchy, eclectic town today. Visit the most haunted places in Salem, like the Hawthorne Hotel, if you dare. Thousands descend upon the area each October for Haunted Happenings, the town’s annual Halloween celebration. Be prepared for crowds.

The popular 90s film Hocus Pocus was filmed here. You can check out each filming location, including Allison’s and Max and Dani’s houses. The nearby Salem Pioneer Village was the site of the witches’ woodsy hideout.

Salem is rich in history, and you’ll be kept busy by museums, exhibits, and notable sites. History buffs might want to read up on the tragic witch trials before visiting; this will help you better understand the dark events of the town’s past and the people involved.

In Salem, fall is definitely in the air. It’s a beautiful and picturesque destination that is great for shopping, dining, and walking. Its proximity to Boston makes it an easy getaway, too. With its position on the coast, Salem is likely to experience peak foliage in mid-to-late October.

Not to miss fall spots in Connecticut

🍁 Connecticut 🍁

🔸Route 7

Northwestern Connecticut’s Litchfield Hills region has sprawling village greens, rolling hills, and views of the Housatonic River. Begin in the coastal town of Norwalk, then continue the trail through Kent Falls State Park. Don’t forget to stop for the waterfalls! Pass through Woodbury, known as the “antiques capital of Connecticut.” End your colorful journey in Litchfield Hills for a classic New England aesthetic explorable on foot, horseback–or even hot air balloon.

🔸Route 9

The Lower Connecticut River Valley has more than enough activities to keep anyone busy in the charming region. Essex, for example, was named “The Perfect Small American Town” in 1,000 Places to See Before You Die. Located across the Connecticut River, the Florence Griswold Museum in Old Lyme is a boarding house-turned-museum where American Impressionist painters like Childe Hassam, Willard Metcalf, and Henry Ward Ranger once lived and worked. It is now a National Historic Landmark with a separate 9,500-square-foot gallery building.

🔸Old Lyme

The best time to check out the fall foliage in most of Connecticut is the second and third week of October, though its season can extend into the first week of November. One of the best places to visit is Old Lyme, a small town along Connecticut’s coast. It is very popular during the summer but still draws visitors during the fall because of its old-growth trees. This makes it a top spot for foliage fans.

Connecticut fall road trip


Located in the middle of Litchfield Hills, this is one of the prettiest areas in the state. There are many farms where you can go pumpkin picking, roam through a corn maze, and indulge in beer and cider tastings.


Visit the historic town of Litchfield for some truly beautiful autumn leaves, which often have the very first views of the season of gorgeous foliage.


This picturesque town of Kent offers some of the best hiking trails through Kent Fall State Park or the nearby Macedonia Brook State Park.

🔸East Haddam

East Haddam is another great town for leaf-peeping during the fall season. Explore the changing leaves along the Connecticut River in Devil’s Hopyard State Park. You will find covered bridges, rocks, streams, and so much more here.

Rhode Island fall spots

🍁 Rhode Island 🍁

🔸Ocean Drive

It may be the smallest state in the country, but every square mile of Rhode Island offers beautiful sights to enjoy. The best way to enjoy Ocean Drive is by bike. Start on the Bellevue Avenue side of the Ocean Drive Loop. This is an 11-mile waterfront route that passes through colorful American yellowwoods, European beeches, and the stately mansions of Bellevue before opening onto Ocean Drive. It offers dual views of the Rhode Island Sound on your left and jaw-dropping colors on your right. End at the equally scenic Newport Harbor, where you can grab a bite to eat at Belle’s Café in the Shipyard for coffee and yacht views. Arrive at dawn or dusk to avoid the crowds.


Bristol offers historic architecture and stunning landscapes, and the local Colt State Park always showcases some of fall’s best colors yearly.

Rhode Island fall spots to see


The capital city of Rhode Island is the perfect spot for a scenic stroll through Roger Williams Park. You’ll love enjoying autumn’s best views while taking in the rolling hillsides.


Ask anyone for a recommendation of where to visit in Rhode Island, and it’s very likely that Newport will be at the top of that list. There’s no wrong time to visit Newport. However, if you want to enjoy the fall foliage, the best time is around the end of October.  During this time, the leaves change colors, and the Newport Mansions put on their spookiest Halloween shows and decorations.

🍁 Maine 🍁

🔸Coastal Route 1

Start your drive in Portland and head north on “Old Route 1” for one of New England’s most scenic coastal drives. Several great stops along the way include Brunswick, Bath, or Rockport. Beautiful seaside mansions, lighthouses, and even late-season lobster rolls will be found. If you need a new pair of Bean boots or want to stock up on flannel for the season, stop in Freeport to visit the L.L. Bean flagship store. End your journey in the quaint town of Camden, where you can capitalize on prime leaf-peeping spots like Merryspring, a 66-acre park and nature center.

🔸Acadia National Park

Northeast of Camden, you will find the stunning 47,000-acre Acadia National Park. Located on Mount Desert Island, this park is a nature lover’s paradise and the epitome of foliage destinations. Take the 27-mile Park Loop Road to enjoy many spots to pull off the road and photograph the foliage. Take in the sweeping views from Cadillac Mountain. The fall colors generally peak between Oct. 13 and 22, but check foliage websites for the most up-to-date information.


The best way to see the changing leaves in this town is by walking around. Bethel also offers hiking access to well-known trails in some conservation areas, including the White Mountain National Forest, Grafton Notch State Park, and the Appalachian Trail. One of the best locations to see wildlife and fall foliage is the Androscoggin River Recreation Trail. Leaves start to change color in this area around September 25th and peak around the first week of October. Its proximity to New Hampshire also makes combining this area with a visit to the White Mountains easy.

Must see spots in the fall in Maine


You’ll see bright reds, oranges, and muted yellows in Millinocket, Maine, around the end of September until about the second week of October this year. Millinocket is the perfect place for those who want to experience the chilly autumn temperatures with the colorful falling leaves. Grab a hot chocolate from a local café before exploring this area.

🔸Bar Harbor

Typically from mid-September until mid-October, Bar Harbor bursts with leaves in all shades of red, orange, yellow, and green. With Acadia National Park so close to the city, you can easily combine a visit to Bar Harbor with a visit to Acadia.


This town is a must-see on your New England fall foliage tour. Head to the Eastern Promenade Trail in Portland for unmatched views of autumnal hues against the blues of the coastal waters.


One of the best spots to take in all that fall has to offer in Maine is the town of Camden. Leaf peepers can head to Camden Hills State Park, home of Mount Battie. The hike is beautiful, and the summit offers an unprecedented view of the colorful treetops.

At the end of the day, watching the sunset over the tranquil, autumn-kissed landscape feels like a dream. Fall in New England; you’ve stolen my heart! Let me know where your favorite New England fall spots are. 

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Kristal Ham

Hi fellow nomads!

Traveler and Photographer

My name is Kristal and I am so happy to have you visit my site! 

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