Fall Itineraries in Connecticut

Cooling temperatures, changing color, and thinning crowds — plans timed for the quieter, more comfortable side of the year.

28 itineraries

Ivy, Green, and Gaslight: Two Autumn Days in New Haven

2 Days · Active Retirees

New Haven, Connecticut

Ivy, Green, and Gaslight: Two Autumn Days in New Haven

4 stops

Stone, Stream, and Sugar Maples: Two Slow Days in the Quiet Corner

2 Days · Active Retirees

Quiet Corner (North/East), Connecticut

Stone, Stream, and Sugar Maples: Two Slow Days in the Quiet Corner

3 stops

Gilded Pages & River Light: Two Unhurried Days in Hartford

2 Days · Active Retirees

Hartford area, Connecticut

Gilded Pages & River Light: Two Unhurried Days in Hartford

5 stops

Ink, Iron, and River Light: 3 Days Alone in Hartford

3 Days · Solo

Hartford area, Connecticut

Ink, Iron, and River Light: 3 Days Alone in Hartford

8 stops

Ivy, Apizza & Amistad: 3 Days Alone in New Haven

3 Days · Solo

New Haven, Connecticut

Ivy, Apizza & Amistad: 3 Days Alone in New Haven

8 stops

Currents & Curiosities: A Family Weekend in Hartford

3 Days · Teen Families

Hartford area, Connecticut

Currents & Curiosities: A Family Weekend in Hartford

8 stops

Stone, Brook & Legend: Three Days in Connecticut's Quiet Corner

3 Days · Teen Families

Quiet Corner (North/East), Connecticut

Stone, Brook & Legend: Three Days in Connecticut's Quiet Corner

6 stops

Ivy, Bones, and Brick: 3 Days in New Haven with Your Teens

3 Days · Teen Families

New Haven, Connecticut

Ivy, Bones, and Brick: 3 Days in New Haven with Your Teens

8 stops

Ivy, Ink, and Apizza: A Gentle 3 Days in New Haven

3 Days · Active Retirees

New Haven, Connecticut

Ivy, Ink, and Apizza: A Gentle 3 Days in New Haven

6 stops

Carousel Mornings & Curious Minds: A Family Weekend in Hartford

2 Days · Young Families

Hartford area, Connecticut

Carousel Mornings & Curious Minds: A Family Weekend in Hartford

4 stops

Stone, Stream, and Hemlock Shadow: Two Days in the Quiet Corner

2 Days · Couples

Quiet Corner (North/East), Connecticut

Stone, Stream, and Hemlock Shadow: Two Days in the Quiet Corner

3 stops

Stone Legends & Streamside Wandering: 2 Days in the Quiet Corner

2 Days · Young Families

Quiet Corner (North/East), Connecticut

Stone Legends & Streamside Wandering: 2 Days in the Quiet Corner

4 stops

Ivy, Amber Light, and Coal-Fired Pie: Two Days in New Haven

2 Days · Couples

New Haven, Connecticut

Ivy, Amber Light, and Coal-Fired Pie: Two Days in New Haven

5 stops

Gaslight and River Light: A Hartford Weekend for Two

2 Days · Couples

Hartford area, Connecticut

Gaslight and River Light: A Hartford Weekend for Two

5 stops

Dinosaurs, Green Grass & Golden Leaves: A Family Weekend in New Haven

2 Days · Young Families

New Haven, Connecticut

Dinosaurs, Green Grass & Golden Leaves: A Family Weekend in New Haven

3 stops

Stone, Stream, and Slow Light: 3 Days in the Quiet Corner

3 Days · Active Retirees

Quiet Corner (North/East), Connecticut

Stone, Stream, and Slow Light: 3 Days in the Quiet Corner

5 stops

Gilded Pages & River Light: Three Unhurried Days in Hartford

3 Days · Active Retirees

Hartford area, Connecticut

Gilded Pages & River Light: Three Unhurried Days in Hartford

7 stops

Stone, Brook, and Hemlock Shadow: Three Days in Connecticut's Quiet Corner

3 Days · Couples

Quiet Corner (North/East), Connecticut

Stone, Brook, and Hemlock Shadow: Three Days in Connecticut's Quiet Corner

4 stops

Ivy, Green Light & Coal-Fired Nights: 3 Days in New Haven

3 Days · Couples

New Haven, Connecticut

Ivy, Green Light & Coal-Fired Nights: 3 Days in New Haven

6 stops

Dinosaurs, Green Grass & Coal-Fired Pies: 3 Days in New Haven with Kids

3 Days · Young Families

New Haven, Connecticut

Dinosaurs, Green Grass & Coal-Fired Pies: 3 Days in New Haven with Kids

4 stops

Gilded Pages & River Light: A Couple's Weekend in Hartford

3 Days · Couples

Hartford area, Connecticut

Gilded Pages & River Light: A Couple's Weekend in Hartford

8 stops

Riverlight & Storybook Streets: 3 Days in Hartford with Little Ones

3 Days · Young Families

Hartford area, Connecticut

Riverlight & Storybook Streets: 3 Days in Hartford with Little Ones

6 stops

Ivy, Bones & Brick: Two Fall Days in New Haven

2 Days · Teen Families

New Haven, Connecticut

Ivy, Bones & Brick: Two Fall Days in New Haven

6 stops

Ink, Atoms & River Light: Two Days in Hartford

2 Days · Teen Families

Hartford area, Connecticut

Ink, Atoms & River Light: Two Days in Hartford

6 stops

Stone, Stream, and Legend: Two Fall Days in the Quiet Corner

2 Days · Teen Families

Quiet Corner (North/East), Connecticut

Stone, Stream, and Legend: Two Fall Days in the Quiet Corner

3 stops

Ivy, Bone, and Brick: Two Days Alone in New Haven

2 Days · Solo

New Haven, Connecticut

Ivy, Bone, and Brick: Two Days Alone in New Haven

4 stops

Stone, Stream, and Solitude: Two Days in the Quiet Corner

2 Days · Solo

Quiet Corner (North/East), Connecticut

Stone, Stream, and Solitude: Two Days in the Quiet Corner

4 stops

Rivers, Rooms, and Ink: Two Days in Hartford's Quiet Corners

2 Days · Solo

Hartford area, Connecticut

Rivers, Rooms, and Ink: Two Days in Hartford's Quiet Corners

6 stops

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