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 Addison Art Gallery and Salt Pond Visitor Center. Step off the beaten path and head to Doane Rock and Gustare Oils and Vinegars. 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 Skaket Beach and stroll through Nauset Beach.

To see where to stay, reviews, traveler tips, and tourist information, refer to the Chatham online tour itinerary planner.

Boston to Chatham is an approximately 2-hour car ride. You can also take a bus. In October in Chatham, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 3rd (Sat) early enough to drive to Newport.

Things to do in Chatham

Outdoors Beaches Parks

Side Trips

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

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 Blithewold Mansion, Gardens & Arboretum and Edward Gorey House. You'll get in some beach time at Sachuest Beach (Second Beach) and Herring Cove Beach. Explore the numerous day-trip ideas around Newport: New Bedford Whaling Museum (in New Bedford), Plymouth (The Jenney & National Monument to the Forefathers) and Sandwich (Heritage Museums & Gardens & Sandwich Glass Museum). And it doesn't end there: pause for some serene contemplation at St. Mary's Catholic Church, visit a coastal fixture at Beavertail Lighthouse and Park, appreciate the history behind Salty the Seahorse, and tour the pleasant surroundings at Fort Adams State Park.

To see more things to do, where to stay, and tourist information, go to the Newport trip planning app.

You can drive from Chatham to Newport in 2 hours. Alternatively, you can take a bus. In October, daily temperatures in Newport can reach °F, while at night they dip to °F. Cap off your sightseeing on the 10th (Sat) early enough to go by car to New Haven.

Things to do in Newport

Museums Historic Sites Parks

Side Trips

Falmouth, Plymouth, Fall River, Sandwich, Sachuest Beach (Second Beach)
Highlights from your plan
Blithewold Mansion, Gardens & Arboretum ©
Blithewold Mansion, Gardens & Arboretum
Edward Gorey House ©
Edward Gorey House
St. Mary's Catholic Church ©
St. Mary's Catholic Church

6
nights
New Haven

New Haven ©
New Haven, in the U.S. Get in touch with nature at Sleeping Giant State Park and West Hartford Reservoir. Get some cultural insight at New England Air Museum and Florence Griswold Museum. Change things up with these side-trips from New Haven: Jones Family Farm (in Shelton), Gillette Castle State Park (in East Haddam) and The Submarine Force Museum (in Groton). There's still lots to do: admire the masterpieces at Hill-Stead Museum, immerse yourself in nature at Hammonasset Beach State Park, shop like a local with Lyman Orchards, and visit a coastal fixture at Stratford Point & Lighthouse.

For reviews, ratings, where to stay, and other tourist information, read our New Haven trip site.

You can drive from Newport to New Haven in 2.5 hours. Other options are to 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. Cap off your sightseeing on the 16th (Fri) early enough to go by car to Lenox.

Things to do in New Haven

Museums Parks Historic Sites

Side Trips

Hartford, Hammonasset Beach State Park, West Hartford Reservoir, Florence Griswold Museum, The Submarine Force Museum
Highlights from your plan
Sleeping Giant State Park ©
Sleeping Giant State Park
Florence Griswold Museum ©
Florence Griswold Museum
New England Air Museum ©
New England Air Museum

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 Bash Bish Falls. Historic Deerfield and The Mount, Edith Wharton's Home will appeal to museum buffs. Change things up with these side-trips from Lenox: Mount Greylock State Reservation (in Lanesboro), Springfield (Dr. Seuss National Memorial Sculpture Garden & Basketball Monument) and Yankee Candle Flagship Store (in South Deerfield). And it doesn't end there: take in the awesome beauty at Monument Mountain, explore the galleries of Ventfort Hall Mansion and Gilded Age Museum, steep yourself in history at Chesterwood Museum, and see the interesting displays at Emily Dickinson Museum.

To see ratings, where to stay, maps, and other tourist information, you can read our Lenox vacation 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 little chillier 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, Springfield, Pittsfield, Stockbridge, Mount Greylock State Reservation
Highlights from your plan
Herman Melville's Arrowhead ©
Herman Melville's Arrowhead
Historic Deerfield ©
Historic Deerfield
Emily Dickinson Museum ©
Emily Dickinson Museum

4
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Get in touch with nature at Mount Greylock and Lye Brook Falls. You'll explore and learn at Bennington Museum and North Adams Museum of History & Science. Explore Bennington's surroundings by going to Natural Bridge State Park (in North Adams), Vermont Country Store (in Weston) and Equinox Mountain (in Arlington). There's still lots to do: stroll the grounds of The Old First Church, whizz through the canopy at some of the top local zipline courses and adventure parks, admire the masterpieces at MASS MoCA, 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, Vermont Country Store, Mount Greylock, Bridge of Flowers
Highlights from your plan
Natural Bridge State Park ©
Natural Bridge State Park
Bennington Museum ©
Bennington Museum
The Old First Church ©
The Old First Church

4
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Your cultural itinerary includes sights like Saint-Gaudens National Historic Site and Calvin Coolidge Homestead. Get outdoors at Mount Tom and Marsh - Billings - Rockefeller National Historical Park. There's still lots to do: steep yourself in history at President Calvin Coolidge State Historic Site, experience rural life at Mac's Maple, snap pictures at Quechee Bridge, and make a trip to Taftsville Covered Bridge.

To see where to stay, other places to visit, reviews, and more tourist information, read Woodstock travel itinerary planner.

Traveling by car from Bennington to Woodstock takes 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to °F, and evening lows to °F. Finish your sightseeing early on the 30th (Fri) so you can drive 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
Mount Tom ©
Mount Tom
President Calvin Coolidge State Historic Site ©
Simon Pearce Mill ©
Simon Pearce Mill

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 Smugglers Notch State Park and Hope Cemetery. Visiting Moss Glen Falls and Toll Rd will get you outdoors. Explore the numerous day-trip ideas around Stowe: Burlington (Burlington Bike Path & Waterfront Park), Shelburne Farms (in Shelburne) and Magic Hat Brewing Company (in South Burlington). There's lots more to do: make a trip to Bragg Farm Sugar House & Gift Shop, experience rural life at Morse Farm Maple Sugarworks, stroll through Stowe Mountain Resort, 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, Magic Hat Brewing Company
Highlights from your plan
Smugglers Notch State Park ©
Smugglers Notch State Park
Hope Cemetery ©
Hope Cemetery
Moss Glen Falls ©
Moss Glen Falls

5
nights
Lincoln

Lincoln ©
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Explore hidden gems such as Sabbaday Falls and Echo Lake Beach. 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: Canterbury Shaker Village (in Canterbury) and Squam Lakes Natural Science Center (in Holderness). There's much more to do: admire the majestic nature at Franconia Notch State Park, look for gifts at Chutters, take in the dramatic natural features at The Basin at Franconia Notch State Park, and look for all kinds of wild species at 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 Winter Sports

Side Trips

Franconia, Littleton, Canterbury Shaker Village, Fairbanks Museum and Planetarium, Museum of the White Mountains
Highlights from your plan
Sabbaday Falls ©
Sabbaday Falls
Canterbury Shaker Village ©
Canterbury Shaker Village
Fairbanks Museum and Planetarium ©
Fairbanks Museum and Planetarium

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 Glen Ellis Falls and Echo Lake State Park. Let the collections at Wright Museum of WWII and Mount Washington Observatory Weather Discovery Center capture your imagination. You'll find plenty of places to visit near North Conway: Castle in the Clouds (in Moultonborough) and Crawford Notch State Park (in Hart's Location). There's still lots to do: take in the dramatic scenery at Jackson Falls, look for gifts at Zeb's General Store, do a tasting at White Mountain Winery, and stroll through Rocky Gorge.

To find more things to do, reviews, photos, and tourist information, read our North Conway trip planning app.

Traveling by car from Lincoln to North Conway takes 1.5 hours. Alternatively, you can take a bus. In November, plan for daily highs up to °F, and evening lows to °F. Finish your sightseeing early on the 13th (Fri) so you can drive to Portland.

Things to do in North Conway

Nature Parks Museums

Side Trips

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

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 Marshall Point Lighthouse Museum and Doubling Point Lighthouse. You'll discover tucked-away gems like Spring Point Ledge Lighthouse and Bowdoin College. Explore the numerous day-trip ideas around Portland: Finnish Church and Heritage House (in South Thomaston), Farnsworth Art Museum (in Rockland) and Pemaquid Point Lighthouse (in Bristol). The adventure continues: kick back and relax at Casco Bay, see the interesting displays at Owls Head Transportation Museum, admire the masterpieces at Ogunquit Museum of American Art, and identify plant and animal life at Rachel Carson National Wildlife Refuge.

To find maps, reviews, ratings, and other tourist information, you can read our Portland trip itinerary maker app.

Drive from North Conway to Portland in 2 hours. Alternatively, you can do a combination of taxi and bus. In November in Portland, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 21st (Sat) early enough to drive to Bar Harbor.

Things to do in Portland

Outdoors Museums Historic Sites

Side Trips

Kennebunkport, Wells, Owls Head Transportation Museum, Marshall Point Lighthouse Museum, Kittery Trading Post
Highlights from your plan
Spring Point Ledge Lighthouse ©
Spring Point Ledge Lighthouse
Marshall Point Lighthouse Museum ©
Marshall Point Lighthouse Museum
Maine State Museum ©
Maine State 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 Bubble Rock and Gorham Mountain Trail. Satisfy your inner culture vulture at The Seal Cove Auto Museum and Rockland Breakwater 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 much more to do: trek along Great Head Trail, enjoy the sand and surf at Sand Beach, stroll around Agamont Park, and take in the dramatic natural features at Otter Cliff.

For ratings, traveler tips, more things to do, and more tourist information, refer to the Bar Harbor trip planner.

You can drive from Portland to Bar Harbor in 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In November, daily temperatures in Bar Harbor can reach °F, while at night they dip to °F. On the 29th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Bar Harbor

Parks Outdoors Trails

Side Trips

Acadia National Park, The Seal Cove Auto Museum, Ship Harbor Nature Trail, Schoodic Point, Camden Hills State Park
Highlights from your plan
Gorham Mountain Trail ©
Gorham Mountain Trail
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Great Head Trail ©
Great Head Trail

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