11 days in New England Itinerary

11 days in New England Itinerary

Created using Inspirock New England trip planner

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Route & dates

11 days in New England Itinerary

Start: Ansonia
Drive:  45​min
1
Litchfield
— 1 day
Drive:  1​h
2
Monterey
— 3 nights
Drive:  4​h
3
Stowe
— 2 nights
Drive:  4​h
4
Kennebunkport
— 2 nights
Drive:  45​min
5
Portland
— 3 nights
Drive:  4​h
End: Ansonia

1
day
Litchfield

Litchfield ©
Litchfield is a town in and former county seat of Litchfield County, Connecticut, United States. On the 4th (Fri), identify plant and animal life at White Memorial Conservation Center, then take in the dramatic scenery at Kent Falls State Park, then take in nature's colorful creations at Hollister House Garden, and finally do a tasting at Haight-Brown Vineyard.

To see photos, maps, reviews, and more tourist information, read our Litchfield online trip itinerary builder .

Ansonia to Litchfield is an approximately 1-hour car ride. October in Litchfield sees daily highs of 63°F and lows of 45°F at night. Finish up your sightseeing early on the 4th (Fri) so you can travel to Monterey.

Things to do in Litchfield

Parks Nature Wineries

Side Trips

Kent Falls State Park, Hollister House Garden
Highlights from your plan
Kent Falls State Park ©
Kent Falls State Park
White Memorial Conservation Center ©
Hollister House Garden ©
Hollister House Garden

3
nights
Monterey

Monterey ©
Monterey is a town in Berkshire County, Massachusetts, United States. Vermont Country Store has been added to your itinerary. On the 5th (Sat), contemplate the waterfront views at Otis Reservoir, stop by Vermont Country Store, and then stroll around Tyringham Cobble. On the 6th (Sun), you'll have a packed day of sightseeing: examine the collection at Bidwell House Museum, delve into the lush surroundings at Beartown State Forest, and then delve into the lush surroundings at Tolland State Forest.

To find ratings, maps, other places to visit, and tourist information, read our Monterey trip itinerary website .

Traveling by car from Litchfield to Monterey takes an hour. Traveling from Litchfield in October, Monterey is a bit cooler at night with lows of 40°F. Finish your sightseeing early on the 7th (Mon) so you can travel to Stowe.

Things to do in Monterey

Parks Nature Shopping

Side Trips

Otis, Vermont Country Store, Tyringham Cobble
Highlights from your plan
Beartown State Forest ©
Beartown State Forest
Bidwell House Museum ©
Bidwell House Museum
Vermont Country Store ©
Vermont Country Store

2
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.
On the 7th (Mon), take your sightseeing to a higher altitude at Mount Mansfield State Forest, view the masterpieces at Remarkable Things at Stowe Craft, and then stroll through Stowe Recreation Path. Keep things going the next day: see the interesting displays at Shelburne Museum, stroll through Burlington Bike Path, and then stroll around Waterfront Park.

To see maps, ratings, traveler tips, and more tourist information, refer to the Stowe online trip itinerary planner .

Drive from Monterey to Stowe in 4 hours. In October, plan for daily highs up to 60°F, and evening lows to 39°F. Wrap up your sightseeing on the 9th (Wed) to allow time to drive to Kennebunkport.

Things to do in Stowe

Parks Outdoors Trails

Side Trips

Burlington, Shelburne Museum
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest
Shelburne Museum ©
Shelburne Museum

2
nights
Kennebunkport

Kennebunkport ©
Kennebunkport is a town in York County, Maine, United States. When in Kennebunkport, make a side trip to see Perkins Cove in Ogunquit, approximately 32 minutes away. There's much more to do: appreciate the extensive heritage of Marginal Way Walkway, kick back and relax at Ogunquit Beach, take a memorable drive along Ocean Ave, and brush up on your military savvy at First Families Kennebunkport Museum.

To find other places to visit, photos, traveler tips, and more tourist information, refer to the Kennebunkport trip planning tool .

Traveling by car from Stowe to Kennebunkport takes 4 hours. Alternatively, you can take a bus; or take a train. In October, plan for daily highs up to 62°F, and evening lows to 38°F. On the 11th (Fri), wrap the sightseeing up by early afternoon so you can drive to Portland.

Things to do in Kennebunkport

Historic Sites Outdoors Scenic Drive

Side Trips

Ogunquit, Nubble Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
St. Ann's Episcopal Church ©
St. Ann's Episcopal Church
Nubble Lighthouse ©
Nubble Lighthouse

3
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.
You'll find plenty of places to visit near Portland: Kancamagus Highway (in North Conway) and Coastal Maine Botanical Gardens (in Boothbay). There's still lots to do: enjoy breathtaking views from Portland Observatory, stop by L.L. Bean Factory Store, stroll through Beth Condon Pathway, and take in the architecture and atmosphere at The Cathedral Of The Immaculate Conception.

To see other places to visit, more things to do, and more tourist information, read Portland trip planner .

Traveling by car from Kennebunkport to Portland takes an hour. Alternatively, you can take a bus; or do a combination of bus and train. In October, plan for daily highs up to 62°F, and evening lows to 43°F. You'll have a few hours on the 14th (Mon) to wrap things up before traveling home.

Things to do in Portland

Parks Outdoors Shopping

Side Trips

Kancamagus Highway, Coastal Maine Botanical Gardens, L.L. Bean Factory Store, Beth Condon Pathway
Highlights from your plan
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
Kancamagus Highway ©
Kancamagus Highway
Portland Observatory ©
Portland Observatory

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