13 Activities
Litchfield Hills Loop: Boston to Litchfield
Starts from
Boston
Transportation
By Car
Guidance
Self-Guided
Activities
13
Duration
2 days
Length
170 mi
Guide details
Starts from
Boston
Transportation
By Car
Guidance
Self-Guided
Duration
2 days
Length
170 mi
Kelsey Perrett
Travel Expert
- Stop and smell the flowers at Hartford's Elizabeth Park.
- Dine inside the former Litchfield Jail.
- Photograph the famous bridge at Lovers Leap State Park.
The Litchfield Hills are one of the most popular destinations in Connecticut, known for their rural scenery, antique shops, and touches of high society. This two-day tour will take road trippers through Connecticut's capital of Hartford and arrive for the night in the classic New England town of Litchfield. The next day, you’ll explore trails, museums, and more in the townships of Kent and Washington.
This road trip visits the traditional lands of the Poquonook, Wangunks, Tunxis, Massacoes, Mohican, Schaghticoke, Paugussett, and Wappinger peoples. Go in summer or fall for the best conditions and scenery.
This road trip visits the traditional lands of the Poquonook, Wangunks, Tunxis, Massacoes, Mohican, Schaghticoke, Paugussett, and Wappinger peoples. Go in summer or fall for the best conditions and scenery.
The Litchfield Hills are one of the most popular destinations in Connecticut, known for their rural scenery, antique shops, and touches of high society. This two-day tour will take road trippers through Connecticut's capital of Hartford and arrive for the night in the classic New England town of Litchfield. The next day, you’ll explore trails, museums, and more in the townships of Kent and Washington.
This road trip visits the traditional lands of the Poquonook, Wangunks, Tunxis, Massacoes, Mohican, Schaghticoke, Paugussett, and Wappinger peoples. Go in summer or fall for the best conditions and scenery.
This road trip visits the traditional lands of the Poquonook, Wangunks, Tunxis, Massacoes, Mohican, Schaghticoke, Paugussett, and Wappinger peoples. Go in summer or fall for the best conditions and scenery.
Kelsey Perrett
Travel Expert
- Stop and smell the flowers at Hartford's Elizabeth Park.
- Dine inside the former Litchfield Jail.
- Photograph the famous bridge at Lovers Leap State Park.
Travel itinerary
7 Activities
Day 1
52 mi0.3 mi
Boston to Litchfield
You’ll head west to the Litchfield Hills to spend the night in the namesake town of Litchfield. But before you make it to the countryside, stop off in the capital city of Hartford to enjoy a few metropolitan highlights.
19:15
6 Activities
Day 2
118 mi
Litchfield to Boston
Spend your morning and afternoon meandering through the Western Connecticut river towns of Kent, Washington, and New Milford before driving back to Boston.
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