The Underrated New England Towns Worth Visiting This Fall

New England
By Ella Brown

Discover the hidden gems of New England that come alive with vibrant colors each fall. From picturesque landscapes to historic charm, these towns offer unique experiences that capture the essence of autumn.

1. Rangeley, Maine (Western Lakes & Mountains)

© Appalachian Trail Conservancy

Nestled in the Western Lakes & Mountains region, Rangeley, Maine, transforms into an autumn paradise. The Rangeley Lakes National Scenic Byway offers breathtaking drives through forests awash in color. The peak foliage typically occurs from late September to mid-October. The plentiful hiking trails and roadside pullouts make it a photographer’s dream.

Explore the town’s official fall roundup of scenic drives, hikes, and local events. From quiet lakeside moments to vibrant community festivals, Rangeley offers a uniquely immersive fall experience.

Don’t forget to capture the striking reflection of the colorful trees in the mirror-like lakes.

2. Greenville, Maine (Moosehead Lake)

© Northeast Whitewater

In Greenville, Maine, the vast expanse of Moosehead Lake mirrors the vibrant hues of autumn foliage. As the largest lake in the state, Moosehead offers unparalleled leaf-peeping opportunities. The Moosehead Lake Scenic Byway around Route 15 is a must-see, offering long, dazzling lake-level views.

Greenville serves as the perfect base for boat rides and hiking adventures amidst the fall splendor. The area is frequently highlighted in Maine’s foliage reports, ensuring a scenic visit.

Whether by boat or by foot, the kaleidoscope of colors in Greenville is a sight that leaves visitors in awe.

3. Harrisville, New Hampshire (Monadnock Region)

© Only In Your State

Harrisville, New Hampshire, is like stepping back in time. This 19th-century mill village, designated a National Historic Landmark, exudes charm with its brick mills and white steeples. As autumn hues sweep through, the village becomes even more enchanting.

Explore the Historic Harrisville’s picturesque walking context and visit the well-preserved mill complex. These features offer a peaceful retreat from the bustle of modern life.

Experience the blend of history and nature, especially when the crimson maples frame the quaint streets and create postcard-perfect scenes.

4. Littleton, New Hampshire (White Mountains Gateway)

© Only In Your State

Littleton, New Hampshire, is a gateway to the White Mountains but stands out on its own during fall. Strolling down Main Street leads to the Riverwalk Covered Bridge over the Ammonoosuc River, a perfect spot for leaf-peepers.

The artsy River District offers a unique vantage point to enjoy the season’s colors without venturing far into the wilderness. As the leaves turn, Littleton becomes a charming blend of art and nature.

Discover the local shops and enjoy the juxtaposition of vibrant foliage against historic architecture, making for an unforgettable autumn experience.

5. Waitsfield & Warren, Vermont (Mad River Valley)

© Yankee Magazine

In the heart of Vermont, Waitsfield and Warren offer a quintessential fall experience in the Mad River Valley. Route 100 meanders through lush landscapes dotted with farm stands and iconic covered bridges.

The weekly market, bustling with local produce and crafts, adds a touch of local flavor to your visit. With reliable and spectacular foliage, the area promises scenic serenity.

Whether exploring the valley’s trails or savoring seasonal delights, the charm of Waitsfield and Warren is as enduring as their picturesque settings.

6. Grafton, Vermont (Southern VT)

© TheTravel

Grafton, Vermont, is a pocket of timeless beauty in Southern Vermont. The walkable village, with restored historic buildings and the iconic Grafton Inn, radiates warmth as the autumn colors blanket the hills.

Trails, small museums, and unique village shops are all within an easy stroll, making it a delightful day trip destination. The vibrant foliage enhances the village’s quaint charm.

Experience the serenity of Grafton’s crimson landscapes, where history and nature merge seamlessly to offer a truly enchanting autumn retreat.

7. Shelburne Falls, Massachusetts (Mohawk Trail)

© Fine Art America

Shelburne Falls, Massachusetts, is home to the stunning Bridge of Flowers, a former trolley bridge turned floral haven. This picturesque spot, framed by the Deerfield River, remains a highlight through October.

Pair the bridge visit with a trip to the Glacial Potholes and discover the indie shops that line the streets. The combination of natural wonders and artisanal crafts makes for an engaging autumn day.

With the foliage as your backdrop, Shelburne Falls offers a rich tapestry of sights, sounds, and experiences that capture the essence of fall.

8. Historic Deerfield, Massachusetts (Connecticut River Valley)

© Jack Schultz – Pixels

Nestled in the heart of the Connecticut River Valley, Historic Deerfield is a living museum that transports visitors back in time. Stroll along the mile-long street lined with preserved colonial-era buildings. Each structure tells a story of early American life, offering a glimpse into the past.

Autumn here is magical, with vibrant foliage framing the village, making it a photographer’s dream. The air is crisp, and the history palpable. Can’t-miss spots include the Deerfield Inn and the Memorial Hall Museum, each offering unique insights into the area’s rich heritage.

9. Essex, Connecticut (Lower Connecticut River)

© Only In Your State

Along the banks of the Lower Connecticut River lies Essex, a picturesque town with a maritime soul. Known for its historical charm and scenic beauty, Essex comes alive in the fall.

The annual Burning of the Ships parade is a highlight, commemorating the British raid of 1814. Stroll through the quaint streets, where each corner reveals another piece of history. Enjoy a river cruise or visit the Connecticut River Museum to dive deeper into the town’s nautical past.

10. Wickford Village (North Kingstown), Rhode Island

© rhodytravels

Wickford Village, part of North Kingstown, offers a delightful mix of history and charm by the sea. This coastal village is known for its beautifully preserved colonial architecture and tranquil harbor.

In fall, Wickford transforms into a picturesque wonderland, with the vibrant colors of the season enhancing its quaint beauty. Visitors can explore boutique shops, art galleries, and enjoy waterfront dining. The harbor, filled with boats, provides a serene backdrop to this enchanting village.