New England Fall Foliage Itinerary
5 Day, 7 Day, 10 Day and 14 Day Itinieraries
Last Updated on October 4, 2024 ⋅ Written by Vanessa Howard ⋅ Edited by Laura Schulthies
Welcome to New England
New England is renowned for its breathtaking fall foliage, where the landscape transforms into a vibrant tapestry of reds, oranges, and yellows. These road trip itineraries will guide you through some of the best spots to experience the natural beauty, charming small towns, scenic parks, iconic covered bridges, and picturesque hikes that New England has to offer.
Contents
5 Day Itinerary
Highlights: Franconia Notch State Park • Kancamagus Highway • Crawford Notch State Park • North Conway and Jackson, NH • Route 100 Scenic Byway • Stowe, Woodstock and Manchester, VT • The Berkshires
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Day 1 of 5 : Boston to White Mountains, New Hampshire
Morning: Boston Departure
- Start your journey in Boston, grabbing a warm cup of coffee before hitting the road.
- Drive north towards the White Mountains in New Hampshire, a journey that takes about 2.5 hours. Along the way, enjoy the evolving landscape as you leave the city behind and enter more rural, forested areas.
Afternoon: Franconia Notch State Park
- Upon arriving in the White Mountains, head straight to Franconia Notch State Park. The park is home to the iconic Flume Gorge, a stunning natural granite gorge extending 800 feet at the base of Mount Liberty.
- Take the Flume Gorge hike (2 miles round trip), where you’ll be surrounded by towering cliffs, covered bridges, waterfalls, and brilliant foliage.
Evening: North Conway
- Continue your drive to the charming town of North Conway, a perfect base for exploring the White Mountains.
- Stroll through the town, visit local shops, and enjoy a cozy dinner at a local restaurant.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 2 of 5 : Exploring the White Mountains
Morning: Kancamagus Highway
- Set out on the Kancamagus Highway, a 34.5-mile scenic byway known for its unparalleled fall foliage views. Along the way, stop at various overlooks, including the Sugar Hill Overlook and the C.L. Graham Wangan Overlook, for panoramic views of the vibrant landscape.
- Visit Sabbaday Falls, a short and easy hike that rewards you with a picturesque waterfall surrounded by colorful trees.
Afternoon: Crawford Notch State Park
- Continue your exploration with a visit to Crawford Notch State Park. The park offers several hiking options, including the relatively easy Arethusa Falls Trail, which leads to one of the state’s tallest waterfalls.
- Don’t miss the historic Willey House Site, where you can learn about the area’s history while taking in the stunning surroundings.
Evening: Jackson
- Drive to the nearby town of Jackson, famous for its picturesque covered bridges, such as the Honeymoon Bridge. Take a leisurely walk around town, and enjoy dinner at a local inn.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 3 of 5 : Vermont's Green Mountains
Morning: Drive to Stowe, Vermont
- Head west towards Vermont, specifically the charming town of Stowe. The drive will take about 2.5 hours, with plenty of opportunities to stop and enjoy the scenic views along the way.
- Once in Stowe, take a gondola ride up Mount Mansfield, Vermont’s highest peak, where you’ll be treated to sweeping views of the Green Mountains decked out in their autumn finery. Make a reservation ahead at the Cliff House Restaurant for lunch with a view!
Afternoon: Smugglers Notch
- Drive through Smugglers Notch, a narrow pass with dramatic cliffs on either side, especially beautiful in the fall.
- Hike the Sterling Pond Trail, a moderate hike that leads to a serene pond surrounded by forested hills ablaze with color.
Evening: Stowe Village
- Return to Stowe and explore the village. Stroll along the quaint streets, visit local shops and galleries, and dine in one of the many excellent restaurants.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 4 of 5 : Exploring Vermont’s Scenic Byways
Morning: Route 100 Scenic Byway
- Begin your day with a drive along Route 100, often referred to as the “backbone of Vermont.” This scenic byway runs through some of the most beautiful and rural parts of the state, offering numerous photo opportunities.
- Stop in the town of Waterbury to visit the Cold Hollow Cider Mill for some fresh apple cider and cider donuts—a quintessential New England fall treat. It’s usually crowded with tourists, but we think it’s still worth a stop. You can also get a flight of hard ciders there!
Afternoon: Covered Bridges and Small Towns
- Continue south to Woodstock, often cited as one of the prettiest towns in America. Explore the village green and covered bridges, and take a short hike in the nearby Marsh-Billings-Rockefeller National Historical Park.
- Visit the nearby Taftsville Covered Bridge, one of the oldest covered bridges in Vermont.
Evening: Stay in Woodstock
- Spend the night in Woodstock, enjoying a relaxing evening in one of the town’s charming inns or bed-and-breakfasts.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 5 of 5 : Southern Vermont to the Berkshires, Massachusetts
Morning: Southern Vermont
- Depart Woodstock and head south towards Manchester, Vermont. Take your time to enjoy the drive, stopping in small towns along the way.
- Explore Hildene, the Lincoln family home, which offers stunning views of the surrounding countryside and beautifully maintained gardens.
Afternoon: The Berkshires
- Continue your journey into the Berkshires of Massachusetts. This region is known for its rolling hills, vibrant arts scene, and stunning fall foliage.
- Visit Mount Greylock State Reservation, where you can drive to the summit of Mount Greylock, the highest point in Massachusetts, for panoramic views of the surrounding valleys and mountains. Hike the short loop trails around the summit or simply enjoy the vistas from the War Memorial Tower.
Evening: Lenox or Stockbridge
- End your trip in the picturesque towns of Lenox or Stockbridge. Enjoy a final evening of New England charm with dinner at a local farm-to-table restaurant.
- If time permits, visit the Norman Rockwell Museum in Stockbridge, which offers a glimpse into classic Americana.
7 Day Itinerary
Highlights: Franconia Notch State Park • Kancamagus Highway • Mount Washington • Crawford Notch State Park • North Conway and Jackson, NH • Smugglers’ Notch and Mount Mansfield • Route 100 Scenic Byway • Stowe, Woodstock, and Manchester, VT • Bennington, VT and Covered Bridges • Mount Greylock • Lenox and Stockbridge, MA
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Day 1 of 7 : Boston to White Mountains, New Hampshire
Morning: Boston Departure
- Begin your journey in Boston, heading north towards the White Mountains in New Hampshire, approximately 2.5 hours away.
- Enjoy the changing landscape as you leave the city and enter rural New England.
Afternoon: Franconia Notch State Park
- Visit Franconia Notch State Park and hike the Flume Gorge (2 miles round trip), a stunning natural granite gorge surrounded by fall foliage.
- Explore the park’s scenic highlights, including the Basin and the Old Man of the Mountain Historic Site.
Evening: North Conway
- Continue to North Conway, a charming town nestled in the White Mountains.
- Stroll through the town and enjoy dinner at a cozy local restaurant.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 2 of 7 : White Mountains, New Hampshire
Morning: Kancamagus Highway
- Drive the Kancamagus Highway, a 34.5-mile scenic byway known for its spectacular fall colors.
- Stop at overlooks such as Sabbaday Falls, where you can take a short hike to a beautiful waterfall.
Afternoon: Mount Washington
- Take the historic Mount Washington Auto Road or the Cog Railway to the summit of Mount Washington, the highest peak in the Northeast, for stunning views.
- Explore the visitor center and learn about the mountain’s weather and history.
Evening: Jackson
- Stay in the nearby town of Jackson, famous for its picturesque covered bridges, including the Honeymoon Bridge.
- Relax with dinner in one of Jackson’s charming inns.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 3 of 7 : Franconia Notch and Crawford Notch, New Hampshire
Morning: Franconia Notch State Park
- Revisit Franconia Notch to hike the Artist’s Bluff Trail, offering panoramic views of Echo Lake and the surrounding mountains.
- Continue exploring the area, including the Cannon Mountain Aerial Tramway.
Afternoon: Crawford Notch State Park
- Head to Crawford Notch State Park and hike the Arethusa Falls Trail to one of New Hampshire’s tallest waterfalls.
- Visit the Willey House Historic Site and enjoy the scenic vistas of the Notch.
Evening: Bretton Woods
- Drive to Bretton Woods for an evening at the historic Omni Mount Washington Resort.
- Enjoy a fine dining experience with a view of Mount Washington.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 4 of 7 : Stowe, Vermont
Morning: Drive to Stowe, VT
- Depart for Stowe, Vermont, a scenic drive of about 2.5 hours.
- Stop at the charming town of Littleton, NH, on your way to explore its quaint downtown and covered bridge.
Afternoon: Mount Mansfield and Smugglers’ Notch
- In Stowe, take the gondola ride up Mount Mansfield, Vermont’s highest peak, for stunning fall views.
- Drive through the dramatic Smugglers’ Notch and hike the Sterling Pond Trail.
Evening: Stowe Village
- Explore Stowe’s charming village, visiting local shops and dining in a cozy restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 5 of 7 : Exploring Central Vermont
Morning: Route 100 Scenic Byway
- Drive along Route 100, one of Vermont’s most scenic byways, through picturesque small towns.
- Stop at Waterbury to visit the Ben & Jerry’s Factory for a sweet treat and Cold Hollow Cider Mill for fresh apple cider and donuts.
Afternoon: Woodstock, VT
- Continue to Woodstock, often called the prettiest town in America.
- Explore the village green, visit the Billings Farm & Museum, and walk across the Taftsville Covered Bridge.
Evening: Stay in Woodstock
- Spend the night in a charming bed-and-breakfast or inn in Woodstock.
- Enjoy a farm-to-table dinner at a local restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 6 of 7 : Southern Vermont to the Berkshires, Massachusetts
Morning: Manchester, VT
- Drive to Manchester, VT, and tour Hildene, the Lincoln family home with its beautiful gardens and views.
- Explore the town’s historic district and boutique shops.
Afternoon: Bennington and Covered Bridges
- Continue to Bennington, VT, where you can visit the Bennington Battle Monument and the Old First Church.
- Explore some of Vermont’s most iconic covered bridges, such as the Silk Road Covered Bridge.
Evening: The Berkshires, MA
- Drive into the Berkshires of Massachusetts, a region known for its rolling hills and vibrant arts scene.
- Settle in the towns of Lenox or Stockbridge for the night.
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Day 7 of 7 : The Berkshires, Massachusetts
Morning: Mount Greylock State Reservation
- Drive to the summit of Mount Greylock, the highest point in Massachusetts, for breathtaking views of the fall foliage.
- Hike the short loop trails around the summit or simply enjoy the vistas from the War Memorial Tower.
Afternoon: Lenox and Stockbridge
- Explore the cultural offerings of Lenox, such as The Mount, Edith Wharton’s historic home, with its stunning gardens and architecture.
- Visit the Norman Rockwell Museum in Stockbridge to see classic American art in a quintessential New England setting.
Evening: Farewell Dinner
- Enjoy a farewell dinner at a farm-to-table restaurant in Lenox or Stockbridge, savoring local New England cuisine.
- Reflect on your journey through the vibrant landscapes and charming towns of New England.
10 Day Itinerary
Highlights: Franconia Notch State Park • Kancamagus Highway • Mount Washington • Crawford Notch State Park • North Conway and Jackson, NH • Lake Winnipesaukee • Smugglers’ Notch and Mount Mansfield • Burlington and Lake Champlain • Route 100 Scenic Byway • Stowe, Woodstock, and Manchester, VT • Bennington, VT and Covered Bridges • Mount Greylock • Lenox and Stockbridge, MA
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Day 1 of 10 : Boston to White Mountains, New Hampshire
Morning: Boston Departure
- Start your journey in Boston, heading north towards the White Mountains in New Hampshire, about 2.5 hours away.
- Enjoy the changing landscape as you leave the city and enter rural New England.
Afternoon: Franconia Notch State Park
- Visit Franconia Notch State Park and hike the Flume Gorge (2 miles round trip), a stunning natural granite gorge surrounded by fall foliage.
- Explore the park’s scenic highlights, including the Basin and the Old Man of the Mountain Historic Site.
Evening: North Conway
- Continue to North Conway, a charming town nestled in the White Mountains.
- Stroll through the town and enjoy dinner at a cozy local restaurant.
Take a look at our New Hampshire Bed & Breakfast Guide
click to see more images
Day 2 of 10 : White Mountains, New Hampshire
Morning: Kancamagus Highway
- Drive the Kancamagus Highway, a 34.5-mile scenic byway known for its spectacular fall colors.
- Stop at overlooks such as Sabbaday Falls, where you can take a short hike to a beautiful waterfall.
Afternoon: Mount Washington
- Take the historic Mount Washington Auto Road or the Cog Railway to the summit of Mount Washington, the highest peak in the Northeast, for stunning views.
- Explore the visitor center and learn about the mountain’s weather and history.
Evening: Jackson
- Stay in the nearby town of Jackson, famous for its picturesque covered bridges, including the Honeymoon Bridge.
- Relax with dinner in one of Jackson’s charming inns.
Take a look at our New Hampshire Bed & Breakfast Guide
click to see more images
Day 3 of 10 : Franconia Notch and Crawford Notch, New Hampshire
Morning: Franconia Notch State Park
- Revisit Franconia Notch to hike the Artist’s Bluff Trail, offering panoramic views of Echo Lake and the surrounding mountains.
- Continue exploring the area, including the Cannon Mountain Aerial Tramway.
Afternoon: Crawford Notch State Park
- Head to Crawford Notch State Park and hike the Arethusa Falls Trail to one of New Hampshire’s tallest waterfalls.
- Visit the Willey House Historic Site and enjoy the scenic vistas of the Notch.
Evening: Bretton Woods
- Drive to Bretton Woods for an evening at the historic Omni Mount Washington Resort.
- Enjoy a fine dining experience with a view of Mount Washington.
Take a look at our New Hampshire Bed & Breakfast Guide
click to see more images
Day 4 of 10 : Lakes Region, New Hampshire
Morning: Drive to Lake Winnipesaukee
- Depart for New Hampshire’s Lakes Region, particularly Lake Winnipesaukee, a scenic drive of about 1.5 hours with incredible fall foliage viewing.
- Explore the town of Meredith, with its charming lakeside setting and local shops.
Afternoon: Lake Activities and Scenic Drives
- Take a scenic boat tour on Lake Winnipesaukee to view the foliage from the water.
- Drive around the lake, stopping at Weirs Beach and the small town of Wolfeboro, known as “The Oldest Summer Resort in America.”
Evening: Stay in Wolfeboro
- Spend the night in Wolfeboro, enjoying a lakeside dinner and the serene autumn atmosphere.
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Day 5 of 10 : Stowe, Vermont
Morning: Drive to Stowe, VT
- Depart for Stowe, Vermont, a scenic drive of about 2.5 hours.
- Stop at the charming town of Littleton, NH, on your way to explore its quaint downtown and covered bridge.
Afternoon: Mount Mansfield and Smugglers’ Notch
- In Stowe, take the gondola ride up Mount Mansfield, Vermont’s highest peak, for stunning fall views.
- Drive through the dramatic Smugglers’ Notch and hike the Sterling Pond Trail.
Evening: Stowe Village
- Explore Stowe’s charming village, visiting local shops and dining in a cozy restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 6 of 10 : Burlington and Lake Champlain, Vermont
Morning: Drive to Burlington, VT
- Head west to Burlington, Vermont’s largest city, located on the shores of Lake Champlain.
- Explore the vibrant Church Street Marketplace, filled with shops, cafes, and street performers.
Afternoon: Lake Champlain
- Take a scenic cruise on Lake Champlain to enjoy the fall colors from the water.
- Visit the Shelburne Museum, a large, open-air museum featuring historic buildings, gardens, and American folk art.
Evening: Stay in Burlington
- Spend the evening exploring Burlington’s waterfront, enjoying dinner with a view of the lake.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 7 of 10 : Route 100 Scenic Byway and Woodstock, Vermont
Morning: Route 100 Scenic Byway
- Depart Burlington and drive along Route 100, one of Vermont’s most scenic byways.
- Stop at Waterbury to visit the Ben & Jerry’s Factory for a sweet treat and Cold Hollow Cider Mill for fresh apple cider and donuts.
Afternoon: Woodstock, VT
- Continue to Woodstock, often called the prettiest town in America.
- Explore the village green, visit the Billings Farm & Museum, and walk across the Taftsville Covered Bridge.
Evening: Stay in Woodstock
- Spend the night in a charming bed-and-breakfast or inn in Woodstock.
- Enjoy a farm-to-table dinner at a local restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
click to see more images
Day 8 of 10 : Southern Vermont and Bennington
Morning: Drive to Manchester, VT
- Head south to Manchester, VT, and tour Hildene, the Lincoln family home with its beautiful gardens and views.
- Explore the town’s historic district and boutique shops.
Afternoon: Bennington and Covered Bridges
- Continue to Bennington, VT, where you can visit the Bennington Battle Monument and the Old First Church.
- Explore some of Vermont’s most iconic covered bridges, such as the Silk Road Covered Bridge and the Paper Mill Village Bridge.
Evening: Stay in Bennington
- Spend the night in Bennington, enjoying the town’s historic charm.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 9 of 10 : The Berkshires, Massachusetts
Morning: Drive to the Berkshires
- Depart Bennington and drive into the Berkshires of Massachusetts, a region known for its rolling hills and vibrant arts scene.
- Visit the Hancock Shaker Village, a living history museum that offers insight into Shaker life and features beautiful fall scenery.
Afternoon: Mount Greylock State Reservation
- Drive to the summit of Mount Greylock, the highest point in Massachusetts, for breathtaking views of the fall foliage.
- Hike the short loop trails around the summit or simply enjoy the vistas from the War Memorial Tower.
Evening: Stay in Lenox
- Stay in the picturesque town of Lenox, known for its cultural attractions and quaint streets.
- Enjoy dinner at a farm-to-table restaurant in town.
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Day 10 of 10 : Lenox and Stockbridge, Massachusetts
Morning: Explore Lenox
- Visit The Mount, Edith Wharton’s historic home, with its stunning gardens and architecture.
- Explore the boutiques and galleries in Lenox’s charming downtown area.
Afternoon: Norman Rockwell Museum in Stockbridge
- Head to nearby Stockbridge to visit the Norman Rockwell Museum, showcasing the iconic American artist’s work.
- Walk through Stockbridge’s historic Main Street, which inspired one of Rockwell’s famous paintings.
Evening: Farewell Dinner
- Enjoy a final dinner in Stockbridge or Lenox , savoring local New England cuisine.
- Reflect on your journey through the vibrant landscapes, historic towns, and natural beauty of New England during its most colorful season.
14 Day Itinerary
Highlights: Portsmouth, NH • Camden and Acadia National Park, ME • Grafton Notch State Park • Kancamagus Highway • North Conway and Jackson, NH • Mount Washington • Smugglers’ Notch and Mount Mansfield • Burlington, VT • Route 100 Scenic Byway • Stowe, Woodstock, and Manchester, VT • Bennington, VT • The Berkshires, MA
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Day 1 of 14 : Boston, Massachusetts to Portsmouth, New Hampshire
Morning: Depart Boston for Portsmouth, NH
- Begin your journey by driving from Boston to the coastal town of Portsmouth, New Hampshire.
- Explore the historic Strawbery Banke Museum, a living history museum that showcases life in the 17th and 18th centuries.
Afternoon: Coastal Exploration
- Stroll along the Portsmouth Harbor or take a harbor cruise and visit Prescott Park for beautiful waterfront views.
- Take a short drive to nearby Rye Beach for a peaceful walk along the shore.
Evening: Stay in Portsmouth
- Enjoy dinner at one of Portsmouth’s many seafood restaurants and explore the town’s vibrant nightlife.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 2 of 14 : Portsmouth to Camden, Maine
Morning: Drive to Camden, ME
- Depart for Camden, Maine, a charming coastal town known for its picturesque harbor and stunning fall foliage.
Afternoon: Explore Camden
- Hike up Mount Battie in Camden Hills State Park for panoramic views of the town, harbor, and Penobscot Bay.
- Visit Camden’s charming downtown, filled with boutiques, cafes, and historic buildings.
Evening: Stay in Camden
- Enjoy dinner at a waterfront restaurant and spend the night in a cozy inn or B&B.
Take a look at our Maine Bed & Breakfast Guide
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Day 3 of 14 : Camden and Rockland, Maine
Morning: Explore Rockland
- Take a short drive to Rockland, ME, and visit the Farnsworth Art Museum, featuring American art with a focus on Maine artists.
- Walk along the Rockland Breakwater for stunning views of the ocean and nearby islands.
Afternoon: Return to Camden
- Return to Camden and take a scenic boat tour of Penobscot Bay, enjoying the fall colors from the water.
- Visit the Camden Harbor Park and Amphitheatre, a beautiful spot to relax and take in the views.
Evening: Stay in Camden
- Spend another evening in Camden, enjoying the town’s laid-back coastal charm.
Take a look at our Maine Bed & Breakfast Guide
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Day 4 of 14 : Camden to Acadia National Park, Maine
Morning: Drive to Acadia National Park
- Head north to Acadia National Park, one of the most beautiful natural areas in the country.
- Check into your accommodations in Bar Harbor, the gateway to Acadia.
Afternoon: Begin Exploring Acadia
- Start your exploration of Acadia with the Park Loop Road, stopping at iconic spots like Thunder Hole, Sand Beach, and Otter Cliffs.
- Take a short hike along the Ocean Path for stunning coastal views.
Evening: Bar Harbor
- Spend the evening in Bar Harbor, enjoying fresh seafood at a local restaurant and taking a walk along the waterfront. Be sure to try the local “bar harbor blonde” oysters!
Take a look at our Bar Harbor Bed & Breakfast Guide
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Day 5 of 14 : Acadia National Park, Maine
Morning: Cadillac Mountain
- Wake up early to drive or hike up Cadillac Mountain, the highest point on the East Coast, to catch the sunrise. Car reservations must be booked in advance here.
- Take in the panoramic views of the surrounding tree-covered islands and ocean.
Afternoon: Jordan Pond and Hiking
- Visit Jordan Pond and hike the Jordan Pond Path, a 3.2-mile trail that offers beautiful views of the Bubbles and the pond.
- Have lunch at the Jordan Pond House, famous for its popovers. Reservations required.
Evening: Bar Harbor
- Spend the evening exploring Bar Harbor’s shops, galleries, and lively downtown area.
Take a look at our Bar Harbor Bed & Breakfast Guide
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Day 6 of 14 : Acadia National Park to Bethel, Maine
Morning: Drive to Bethel, ME
- Leave Acadia and head west to the charming mountain town of Bethel, Maine.
- Check into a cozy lodge or B&B in the area.
Afternoon: Explore Grafton Notch State Park
- Spend the afternoon exploring Grafton Notch State Park, known for its stunning fall colors and scenic waterfalls.
- Hike to Screw Auger Falls and Mother Walker Falls for beautiful views.
Evening: Stay in Bethel
- Enjoy dinner at a local restaurant in Bethel and relax in the peaceful mountain setting.
Take a look at our Maine Bed & Breakfast Guide
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Day 7 of 14 : Bethel to North Conway, New Hampshire
Morning: Drive to North Conway, NH
- Take a scenic drive from Bethel to North Conway, New Hampshire, through the White Mountains.
- Arrive in North Conway, a hub for exploring the White Mountains.
Afternoon: Kancamagus Highway
- Drive the Kancamagus Highway, a 34.5-mile scenic byway known for its spectacular fall colors.
- Stop at overlooks such as Sabbaday Falls and Rocky Gorge for short hikes and photo opportunities.
Evening: Stay in North Conway
- Explore North Conway’s charming downtown and enjoy dinner at a local eatery.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 8 of 14 : North Conway and Mount Washington, New Hampshire
Morning: Mount Washington
- Take the historic Mount Washington Auto Road or the Cog Railway to the summit of Mount Washington, the highest peak in the Northeast, for stunning views.
- Explore the visitor center and learn about the mountain’s weather and history.
Afternoon: Crawford Notch State Park
- Head to Crawford Notch State Park and hike the Arethusa Falls Trail to one of New Hampshire’s tallest waterfalls.
- Visit the Willey House Historic Site and enjoy the scenic vistas of the Notch.
Evening: Jackson, NH
- Stay in the nearby town of Jackson, famous for its picturesque covered bridges, including the Honeymoon Bridge.
- Relax with dinner in one of Jackson’s charming inns.
Take a look at our New Hampshire Bed & Breakfast Guide
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Day 9 of 14 : North Conway to Stowe, Vermont
Morning: Drive to Stowe, VT
- Depart for Stowe, Vermont, a scenic drive through the White Mountains and into the Green Mountains.
- Stop at the charming town of Littleton, NH, on your way to explore its quaint downtown and covered bridge.
Afternoon: Mount Mansfield and Smugglers’ Notch
- Upon arrival in Stowe, take the gondola ride up Mount Mansfield, Vermont’s highest peak, for stunning fall views.
- Drive through the dramatic Smugglers’ Notch and hike the Sterling Pond Trail.
Evening: Stowe Village
- Explore Stowe’s charming village, visiting local shops and dining in a cozy restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 10 of 14 : Stowe to Burlington, Vermont
Morning: Drive to Burlington, VT
- Head west to Burlington, Vermont’s largest city, located on the shores of Lake Champlain.
- Explore the vibrant Church Street Marketplace, filled with shops, cafes, and street performers.
Afternoon: Lake Champlain
- Take a scenic cruise on Lake Champlain to enjoy the fall colors from the water.
- Visit the Shelburne Museum, a large, open-air museum featuring historic buildings, gardens, and American folk art.
Evening: Stay in Burlington
- Spend the evening exploring Burlington’s waterfront, enjoying dinner with a view of the lake.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 11 of 14 : Route 100 Scenic Byway and Woodstock, Vermont
Morning: Route 100 Scenic Byway
- Depart Burlington and drive along Route 100, one of Vermont’s most scenic byways.
- Stop at Waterbury to visit the Ben & Jerry’s Factory for a sweet treat and Cold Hollow Cider Mill for fresh apple cider and donuts.
Afternoon: Woodstock, VT
- Continue to Woodstock, often called the prettiest town in America.
- Explore the village green, visit the Billings Farm & Museum, and walk across the Taftsville Covered Bridge.
Evening: Stay in Woodstock
- Spend the night in a charming bed-and-breakfast or inn in Woodstock.
- Enjoy a farm-to-table dinner at a local restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
click to see more images
Day 12 of 14 : Southern Vermont and Manchester
Morning: Drive to Manchester, VT
- Head south to Manchester, VT, and tour Hildene, the Lincoln family home with its beautiful gardens and views.
- Explore the town’s historic district and boutique shops.
Afternoon: Outdoor Activities
- Enjoy a hike in the nearby Green Mountain National Forest, or visit Equinox Mountain for stunning fall foliage views.
- Stroll through Manchester’s designer outlets for some shopping.
Evening: Stay in Manchester
- Spend the night in Manchester, enjoying the town’s historic charm and dining at a local restaurant.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 13 of 14 : Manchester to Bennington, Vermont
Morning: Drive to Bennington, VT
- Head further south to Bennington, VT, and visit the Bennington Battle Monument and the Old First Church.
- Explore some of Vermont’s most iconic covered bridges, such as the Silk Road Covered Bridge and the Paper Mill Village Bridge.
Afternoon: Bennington Exploration
- Discover the Bennington Museum, home to a large collection of Grandma Moses paintings and local history exhibits.
- Take a leisurely drive through the surrounding countryside, enjoying the fall colors.
Evening: Stay in Bennington
- Spend the night in Bennington, relaxing in the town’s peaceful setting.
Take a look at our Vermont Bed & Breakfasts Guide and our Vermont Hotel Guide
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Day 14 of 14 : The Berkshires, Massachusetts
Morning: Drive to the Berkshires
- Depart Bennington and drive into the Berkshires of Massachusetts, a region known for its rolling hills and vibrant arts scene.
- Visit the Hancock Shaker Village, a living history museum that offers insight into Shaker life and features beautiful fall scenery.
Afternoon: Mount Greylock State Reservation
- Drive to the summit of Mount Greylock, the highest point in Massachusetts, for breathtaking views of the fall foliage.
- Hike the short loop trails around the summit or simply enjoy the vistas from the War Memorial Tower.
Evening: Stay in Lenox
- Stay in the picturesque town of Lenox, known for its cultural attractions and quaint streets.
- Enjoy dinner at a farm-to-table restaurant in town, reflecting on your journey through New England’s stunning fall landscapes.
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A Connecticut getaway is a bit like taking a step back in time, and this charming New England state is dotted with coastal towns and rural villages. Keep reading as we take you through Connecticut’s best bed and breakfasts.
Newport Bed & Breakfast Guide
Staying in one of Newport, Rhode Island’s many bed and breakfasts or inns allows you to step back in time and enjoy an intimate experience. Bed and breakfasts in this area maintain Newport’s historical beauty, providing guests with both excellent service and comfort.
Maine Bed & Breakfast Guide
Maine is known for its ruggedly beautiful coastline, charming villages, lighthouses, lobster boats dotting the waters, and warm hospitality. Each of our 15 best bed and breakfasts in Maine offer a unique blend of homey yet luxurious accommodations, personalized service, and delectable breakfasts.
Bar Harbor Bed & Breakfast Guide
With fantastic restaurants, nearby Acadia National Park, and all of the lobster you can handle, it’s no wonder Bar Harbor is one of the East Coast’s most popular destinations. Here are the best Bed & Breakfasts in Bar Harbor, Maine!
New Hampshire In The Fall Guide
New Hampshire delivers stunningly colorful fall foliage, and no autumn trip to the northeast is complete without visiting the Granite State. Keep reading our New Hampshire in the fall guide for quintessential fall activities, when to visit, and the best things to do.
Portland Maine Bed & Breakfast Guide
Looking for a Portland B & B? Portland is a small coastal city in Maine with great food, fun local culture and gorgeous scenery. Here are some of the best bed & breakfasts in Portland.
Vermont Hotel Guide
Vermont offers many excellent accommodations, including boutique hotels, charming bed and breakfasts, and expansive, luxurious resorts. Choosing the right place to drop your bags and relax during your vacation in Vermont has never been easier. Keep reading for the best Vermont hotels and resorts that fit your tastes and budget.
Vermont Bed & Breakfast Guide
Vermont is rich with historic covered bridges, vibrant foliage, cider donuts and quaint country stores. Here are the best Vermont bed & breakfasts for your stay.
Vermont In The Fall Guide
The Green Mountain State shines in every season, but there is something special about Vermont in the fall. Keep reading our Vermont in the fall guide for quintessential fall activities, when to visit, and the best things to do.