Winter Itineraries in Connecticut

Shorter days and quieter destinations — plans built around the season's own pace, indoors and out.

13 itineraries

Frost, Falls & Firelight: 4 Days in the Litchfield Hills

4 Days · Couples

Litchfield Hills (North/South), Connecticut

Frost, Falls & Firelight: 4 Days in the Litchfield Hills

7 stops

Snow Quiet & Steeples: 4 Days in the Litchfield Hills

4 Days · Young Families

Litchfield Hills (North/South), Connecticut

Snow Quiet & Steeples: 4 Days in the Litchfield Hills

6 stops

Frost, Falls & Forest Quiet: 3 Solo Days in the Litchfield Hills

3 Days · Solo

Litchfield Hills (North/South), Connecticut

Frost, Falls & Forest Quiet: 3 Solo Days in the Litchfield Hills

6 stops

Frost, Falls & Forest: A Winter Family Weekend in Litchfield Hills

3 Days · Teen Families

Litchfield Hills (North/South), Connecticut

Frost, Falls & Forest: A Winter Family Weekend in Litchfield Hills

6 stops

Village Greens & Winter Woods: Two Unhurried Days in the Litchfield Hills

2 Days · Active Retirees

Litchfield Hills (North/South), Connecticut

Village Greens & Winter Woods: Two Unhurried Days in the Litchfield Hills

3 stops

Snow-Quiet Villages: A Gentle Winter Weekend in Litchfield Hills

2 Days · Young Families

Litchfield Hills (North/South), Connecticut

Snow-Quiet Villages: A Gentle Winter Weekend in Litchfield Hills

4 stops

Slow Hills, Soft Light: 3 Winter Days in Litchfield Hills

3 Days · Active Retirees

Litchfield Hills (North/South), Connecticut

Slow Hills, Soft Light: 3 Winter Days in Litchfield Hills

6 stops

Snow Days & Fireside Villages: 3 Days in the Litchfield Hills

3 Days · Young Families

Litchfield Hills (North/South), Connecticut

Snow Days & Fireside Villages: 3 Days in the Litchfield Hills

6 stops

Frost, Falls, and Fireside: Two Winter Days in Litchfield Hills

2 Days · Couples

Litchfield Hills (North/South), Connecticut

Frost, Falls, and Fireside: Two Winter Days in Litchfield Hills

4 stops

Frost, Falls, and Forest Silence: A Solo Winter Wander Through Litchfield Hills

2 Days · Solo

Litchfield Hills (North/South), Connecticut

Frost, Falls, and Forest Silence: A Solo Winter Wander Through Litchfield Hills

4 stops

Frost, Falls & Forest Light: A Winter Weekend in the Litchfield Hills

2 Days · Teen Families

Litchfield Hills (North/South), Connecticut

Frost, Falls & Forest Light: A Winter Weekend in the Litchfield Hills

4 stops

Frost, Falls & Fireside: 3 Days in the Litchfield Hills

3 Days · Couples

Litchfield Hills (North/South), Connecticut

Frost, Falls & Fireside: 3 Days in the Litchfield Hills

6 stops

Frost, Falls & Forest: Four Winter Days in Litchfield Hills

4 Days · Teen Families

Litchfield Hills (North/South), Connecticut

Frost, Falls & Forest: Four Winter Days in Litchfield Hills

9 stops

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