60 days in New England Itinerary

60 days in New England Itinerary

Created using Inspirock New England trip planner

©
Plan created by another user.Make it yours

Route & dates

1
Chatham
— 2 nights
2
Newport
— 7 nights
3
New Haven
— 6 nights
4
Lenox
— 6 nights
5
Bennington
— 4 nights
6
Woodstock
— 4 nights
7
Stowe
— 5 nights
8
Lincoln
— 5 nights
9
North Conway
— 4 nights
10
Portland
— 8 nights
11
Bar Harbor, Mount Desert Island
— 8 nights

2
nights
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Museum-lovers will appreciate Salt Pond Visitor Center and Addison Art Gallery. Step off the beaten path and head to Cape Cod National Seashore and Chatham Lighthouse Beach. When in Chatham, make a side trip to see Nauset Lighthouse in Eastham, approximately Eastham away. Next up on the itinerary: kick back and relax at Nauset Beach, look for gifts at Gustare Oils and Vinegars, stroll through Skaket Beach, and contemplate the long history of Doane Rock.

To find maps, reviews, ratings, and tourist information, read Chatham road trip planner.

Boston to Chatham is an approximately 2-hour car ride. You can also take a bus. In October, daily temperatures in Chatham can reach °F, while at night they dip to °F. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Newport.

Things to do in Chatham

Parks Outdoors Beaches

Side Trips

Eastham, Orleans, Cape Cod National Seashore
Highlights from your plan
Nauset Beach ©
Nauset Beach
Skaket Beach ©
Skaket Beach
Cape Cod National Seashore ©
Cape Cod National Seashore

7
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Do some cultural sightseeing at Lizzie Borden House and Rosecliff. You'll get in some beach time at Sachuest Beach (Second Beach) and Herring Cove Beach. Explore the numerous day-trip ideas around Newport: Blithewold Mansion, Gardens & Arboretum (in Bristol), New Bedford Whaling Museum (in New Bedford) and Sandwich (Heritage Museums & Gardens & Sandwich Glass Museum). There's much more to do: steep yourself in history at Chateau-sur-Mer, admire the majestic nature at National Monument to the Forefathers, browse the exhibits of International Tennis Hall of Fame, and take an in-depth tour of The Jenney.

To see more things to do, maps, traveler tips, and tourist information, read Newport trip itinerary maker app.

Traveling by car from Chatham to Newport takes 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 10th (Sat) early enough to drive to New Haven.

Things to do in Newport

Museums Historic Sites Parks

Side Trips

Falmouth, Plymouth, Fall River, Sandwich, Herring Cove Beach
Highlights from your plan
New Bedford Whaling Museum ©
New Bedford Whaling Museum
Lizzie Borden House ©
Lizzie Borden House
Beavertail Lighthouse and Park ©
Beavertail Lighthouse and Park

6
nights
New Haven

New Haven ©
New Haven, in the U.S. Get in touch with nature at Gillette Castle State Park and Talcott Mountain State Park. Get some cultural insight at The Submarine Force Museum and Wadsworth Atheneum Museum of Art. Change things up with these side-trips from New Haven: Harriet Beecher Stowe Center (in Hartford), Jones Family Farm (in Shelton) and Florence Griswold Museum (in Old Lyme). There's much more to do: see the interesting displays at New England Air Museum, admire the masterpieces at Hill-Stead Museum, kick back and relax at Hammonasset Beach State Park, and hike along West Hartford Reservoir.

Make your New Haven itinerary with Inspirock to find out what to see and where to go.

Traveling by car from Newport to New Haven takes 2.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In October in New Haven, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 16th (Fri) to allow time to drive to Lenox.

Things to do in New Haven

Museums Parks Historic Sites

Side Trips

Hartford, Lyman Orchards, Hill-Stead Museum, Sleeping Giant State Park, Gillette Castle State Park
Highlights from your plan
Gillette Castle State Park ©
Gillette Castle State Park
The Submarine Force Museum ©
The Submarine Force Museum
Yale University Art Gallery ©
Yale University Art Gallery

6
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Get in touch with nature at Kent Falls State Park and Monument Mountain. The Mount, Edith Wharton's Home and Yankee Candle Flagship Store will appeal to museum buffs. Change things up with these side-trips from Lenox: Mount Greylock State Reservation (in Lanesboro), Historic Deerfield (in Deerfield) and Springfield (Dr. Seuss National Memorial Sculpture Garden & Basketball Monument). There's lots more to do: get engrossed in the history at Hancock Shaker Village, trek along Ashuwillticook Rail Trail, admire the landmark architecture of Ventfort Hall Mansion and Gilded Age Museum, and steep yourself in history at Chesterwood Museum.

To see traveler tips, ratings, where to stay, and tourist information, refer to the Lenox trip planner.

Traveling by car from New Haven to Lenox takes 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. Prepare for a bit cooler weather when traveling from New Haven in October: high temperatures in Lenox hover around °F and lows are around °F. Wrap up your sightseeing on the 22nd (Thu) to allow time to drive to Bennington.

Things to do in Lenox

Historic Sites Museums Parks

Side Trips

Great Barrington, Pittsfield, Stockbridge, Springfield, Mount Greylock State Reservation
Highlights from your plan
Herman Melville's Arrowhead ©
Herman Melville's Arrowhead
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home
Hancock Shaker Village ©
Hancock Shaker Village

4
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Get in touch with nature at Zipline and Equinox Mountain. You'll explore and learn at MASS MoCA and Bennington Museum. Explore Bennington's surroundings by going to North Adams (Natural Bridge State Park & North Adams Museum of History & Science), Mount Greylock (in Adams) and Vermont Country Store (in Weston). There's still lots to do: stroll the grounds of The Old First Church, get great views at Bennington Battle Monument, take in the dramatic scenery at Lye Brook Falls, and tour the pleasant surroundings at Bridge of Flowers.

To find more things to do, maps, where to stay, and tourist information, go to the Bennington online vacation planner.

Drive from Lenox to Bennington in 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to °F, and evening lows to °F. Finish up your sightseeing early on the 26th (Mon) so you can go by car to Woodstock.

Things to do in Bennington

Parks Nature Museums

Side Trips

North Adams, Arlington, Bridge of Flowers, Zipline, Mount Greylock
Highlights from your plan
Natural Bridge State Park ©
Natural Bridge State Park
MASS MoCA ©
MASS MoCA
Zipline

4
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Your cultural itinerary includes sights like Billings Farm & Museum and Simon Pearce Mill. Get outdoors at Quechee Gorge and Marsh - Billings - Rockefeller National Historical Park. Step out of Woodstock with an excursion to Saint-Gaudens National Historic Site in Cornish--about 34 minutes away. The adventure continues: take in the awesome beauty at Mount Tom, relax in the rural setting at Sugarbush Farm, snap pictures at Taftsville Covered Bridge, and contemplate the long history of Calvin Coolidge Homestead.

To see traveler tips, reviews, and more tourist information, read Woodstock attractions website.

Drive from Bennington to Woodstock in 2 hours. Alternatively, you can take a bus. In October in Woodstock, expect temperatures between °F during the day and °F at night. Finish up your sightseeing early on the 30th (Fri) so you can go by car to Stowe.

Things to do in Woodstock

Historic Sites Nature Parks

Side Trips

Quechee, Plymouth, Mac's Maple, Saint-Gaudens National Historic Site
Highlights from your plan
Quechee Gorge ©
Quechee Gorge
Billings Farm & Museum ©
Billings Farm & Museum

5
nights
Stowe

Stowe ©
Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Your inner history buff will appreciate Shelburne Farms and Hope Cemetery. Visiting Stowe Mountain Resort and Trapp Family Lodge Outdoor Center will get you outdoors. Explore the numerous day-trip ideas around Stowe: Montpelier (Morse Farm Maple Sugarworks & Bragg Farm Sugar House & Gift Shop), Burlington (Burlington Bike Path & Waterfront Park) and Magic Hat Brewing Company (in South Burlington). There's lots more to do: explore and take pictures at Toll Rd, admire the sheer force of Moss Glen Falls, go deep underground at Rock of Ages Granite Quarry, and stop by Cabot Farmers' Store.

Use Inspirock's suggestions to plan your Stowe trip and find the best activities and attractions for your vacation.

Getting from Woodstock to Stowe by car takes about 1.5 hours. Other options: do a combination of bus and train; or do a combination of taxi and train. In October, daytime highs in Stowe are °F, while nighttime lows are °F. Cap off your sightseeing on the 4th (Wed) early enough to go by car to Lincoln.

Things to do in Stowe

Parks Outdoors Historic Sites

Side Trips

Montpelier, Burlington, Barre, Shelburne Farms, Cabot Farmers' Store
Highlights from your plan
Stowe Mountain Resort ©
Stowe Mountain Resort
Shelburne Farms ©
Shelburne Farms
Mount Mansfield State Forest ©
Mount Mansfield State Forest

5
nights
Lincoln

Lincoln ©
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Explore hidden gems such as The Basin at Franconia Notch State Park and Loon Mountain Resort. You'll explore and learn at Fairbanks Museum and Planetarium and Museum of the White Mountains. Get out of town with these interesting Lincoln side-trips: Squam Lakes Natural Science Center (in Holderness) and Canterbury Shaker Village (in Canterbury). There's much more to do: enjoy the sand and surf at Echo Lake Beach, take in the dramatic scenery at Sabbaday Falls, immerse yourself in nature at Franconia Notch State Park, and walk around Lost River Gorge and Boulder Caves.

To find reviews, traveler tips, more things to do, and tourist information, go to the Lincoln trip itinerary builder.

Getting from Stowe to Lincoln by car takes about 2 hours. Other options: take a bus; or take a bus. In November, daytime highs in Lincoln are °F, while nighttime lows are °F. Cap off your sightseeing on the 9th (Mon) early enough to go by car to North Conway.

Things to do in Lincoln

Parks Outdoors Tours

Side Trips

Franconia, Littleton, Sabbaday Falls, Lost River Gorge and Boulder Caves, Fairbanks Museum and Planetarium
Highlights from your plan
Franconia Notch State Park ©
Franconia Notch State Park
The Basin at Franconia Notch State Park ©
The Basin at Franconia Notch State Park
Canterbury Shaker Village ©
Canterbury Shaker Village

4
nights
North Conway

North Conway ©
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Eschew the tourist crowds and head to Cathedral Ledge and Wright Museum of WWII. Escape the urban bustle at Glen Ellis Falls and Echo Lake State Park. Explore North Conway's surroundings by going to Castle in the Clouds (in Moultonborough) and Crawford Notch State Park (in Hart's Location). There's still lots to do: look for gifts at Zeb's General Store, take your sightseeing to a higher altitude at Rocky Gorge, take in the dramatic scenery at Arethusa Falls, and steep yourself in history at Russell-Colbath Homestead.

To see reviews, other places to visit, ratings, and more tourist information, use the North Conway road trip planning site.

Drive from Lincoln to North Conway in 1.5 hours. Alternatively, you can take a bus. In November, plan for daily highs up to °F, and evening lows to °F. Cap off your sightseeing on the 13th (Fri) early enough to go by car to Portland.

Things to do in North Conway

Nature Parks Wildlife

Side Trips

Conway, Jackson, Hart's Location, Castle in the Clouds, White Mountain National Forest
Highlights from your plan
Arethusa Falls ©
Arethusa Falls
White Mountain National Forest ©
White Mountain National Forest
Wright Museum of WWII ©
Wright Museum of WWII

8
nights
Portland

Portland ©
Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Your inner history buff will appreciate Pemaquid Point Lighthouse and Farnsworth Art Museum. You'll discover tucked-away gems like Allagash Brewing Company and Maine Maritime Museum. Explore the numerous day-trip ideas around Portland: Finnish Church and Heritage House (in South Thomaston), Wells (Wells Beach & Rachel Carson National Wildlife Refuge) and Kennebunkport (St. Anthony's Monastery, Ocean Ave, &more). Next up on the itinerary: admire the masterpieces at Ogunquit Museum of American Art, see the interesting displays at Owls Head Transportation Museum, cast your line with a fishing tour, and enjoy the sea views from Spring Point Ledge Lighthouse.

To find maps, where to stay, photos, and more tourist information, use the Portland journey maker app.

You can drive from North Conway to Portland in 2 hours. Alternatively, you can do a combination of taxi and bus. In November, daytime highs in Portland are °F, while nighttime lows are °F. Finish your sightseeing early on the 21st (Sat) so you can drive to Bar Harbor.

Things to do in Portland

Outdoors Museums Historic Sites

Side Trips

Kennebunkport, Wells, Finnish Church and Heritage House, Maine State Museum, Strawbery Banke Museum
Highlights from your plan
Farnsworth Art Museum ©
Farnsworth Art Museum
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse
Owls Head Transportation Museum ©
Owls Head Transportation Museum

8
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. You'll explore the less-touristy side of things at Rockland Breakwater Light and Sand Beach. Satisfy your inner culture vulture at The Seal Cove Auto Museum and Egg Rock Light. Explore Bar Harbor's surroundings by going to Ship Harbor Nature Trail (in Bass Harbor), Schoodic Point (in Winter Harbor) and Camden Hills State Park (in Camden). There's still lots to do: trek along Precipice Trail, tour the pleasant surroundings at Bubble Rock, explore the striking landscape at Schoodic Peninsula, and get a new perspective on things with Boat Tours & Water Sports.

For photos, maps, reviews, and more tourist information, you can read our Bar Harbor online travel planner.

Traveling by car from Portland to Bar Harbor takes 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In November, daytime highs in Bar Harbor are °F, while nighttime lows are °F. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow time for travel back home.

Things to do in Bar Harbor

Parks Outdoors Trails

Side Trips

Acadia National Park, Rockland Breakwater Light, Ship Harbor Nature Trail, Schoodic Point, Camden Hills State Park
Highlights from your plan
Camden Hills State Park ©
Camden Hills State Park
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Rockland Breakwater Light ©
Rockland Breakwater Light

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