11 days in New England Itinerary

11 days in New England Itinerary

Created using Inspirock New England trip planner

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Make it your trip
Drive
1
Litchfield
— 1 day
Drive
2
Monterey
— 3 nights
Drive
3
Stowe
— 2 nights
Drive
4
Kennebunkport
— 2 nights
Drive
5
Portland
— 3 nights
Drive

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Litchfield

— 1 day
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 admire the sheer force of Kent Falls State Park, then admire the natural beauty at Hollister House Garden, and finally do a tasting at Haight-Brown Vineyard.

To see ratings, photos, traveler tips, and tourist information, read Litchfield holiday planning tool.

Ansonia to Litchfield is an approximately 1-hour car ride. In October in Litchfield, expect temperatures between 63°F during the day and 45°F at night. Finish your sightseeing early on the 4th (Fri) so you can travel to Monterey.

Things to do in Litchfield

Parks · Nature · Wineries · Wildlife

Side Trips

Monterey

— 3 nights
Monterey is a town in Berkshire County, Massachusetts, United States. Your day by day itinerary now includes Vermont Country Store. On the 5th (Sat), contemplate the waterfront views at Otis Reservoir, then stop by Vermont Country Store, and then stroll around Tyringham Cobble. Here are some ideas for day two: examine the collection at Bidwell House Museum, take a peaceful walk through Beartown State Forest, and then delve into the lush surroundings at Tolland State Forest.

To see photos, where to stay, reviews, and tourist information, go to the Monterey trip app.

Traveling by car from Litchfield to Monterey takes an hour. Plan for a bit cooler nights when traveling from Litchfield in October since evenings lows in Monterey dip to 40°F. Wrap up your sightseeing on the 7th (Mon) early enough to travel to Stowe.

Things to do in Monterey

Parks · Nature · Shopping · Museums

Side Trips

Stowe

— 2 nights

The Ski Capital of the East

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.
Kick off your visit on the 7th (Mon): take in the awesome beauty at Mount Mansfield State Forest, view the masterpieces at Remarkable Things at Stowe Craft, and then hike along Stowe Recreation Path. On the next day, examine the collection at Shelburne Museum, hike along Burlington Bike Path, and then stroll around Waterfront Park.

For photos, reviews, traveler tips, and other tourist information, read Stowe online itinerary builder.

Drive from Monterey to Stowe in 4 hours. Expect a daytime high around 60°F in October, and nighttime lows around 39°F. Cap off your sightseeing on the 9th (Wed) early enough to go by car to Kennebunkport.

Things to do in Stowe

Parks · Outdoors · Trails · Museums

Side Trips

Kennebunkport

— 2 nights
Kennebunkport is a town in York County, Maine, United States. Get out of town with these interesting Kennebunkport side-trips: Nubble Lighthouse (in York) and Perkins Cove (in Ogunquit). There's still lots to do: appreciate the extensive heritage of Marginal Way Walkway, stroll through Ogunquit Beach, brush up on your military savvy at First Families Kennebunkport Museum, and cruise along Walker's Point.

For other places to visit, traveler tips, ratings, and more tourist information, use the Kennebunkport day trip website.

You can drive from Stowe to Kennebunkport in 4 hours. Alternatively, you can take a bus; or do a combination of train and bus. October in Kennebunkport sees daily highs of 62°F and lows of 38°F at night. Wrap up your sightseeing by early afternoon on the 11th (Fri) to allow time for the car ride to Portland.

Things to do in Kennebunkport

Outdoors · Historic Sites · Scenic Drive · Parks

Side Trips

Portland

— 3 nights

The Forest City

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.
Step out of Portland to go to North Conway and see Kancamagus Highway, which is approximately 1h 25 min away. There's lots more to do: admire the natural beauty at Coastal Maine Botanical Gardens, explore the landscape on two wheels at Beth Condon Pathway, take in panoramic vistas at Portland Observatory, and pause for some serene contemplation at The Cathedral Of The Immaculate Conception.

To see ratings, where to stay, other places to visit, and more tourist information, read Portland visit planner.

Drive from Kennebunkport to Portland in an hour. Alternatively, you can take a bus; or do a combination of bus and train. In October in Portland, expect temperatures between 62°F during the day and 43°F at night. On the 14th (Mon), you'll have the morning to explore before heading back home.

Things to do in Portland

Parks · Shopping · Outdoors · Scenic Drive

Side Trips