2 Days · Solo
Gold Coast (Greenwich area), Connecticut
Salt Air & Storefronts: Two Days on Greenwich's Gold Coast
4 stops
2 Days · Teen Families
Gold Coast (Greenwich area), Connecticut
Salt Air & Sidewalk Cafés: 2 Days on Greenwich's Gold Coast
4 stops
2 Days · Solo
Litchfield Hills (North/South), Connecticut
Ridgeline & Waterfall Light: A Solo Wander Through the Litchfield Hills
6 stops
2 Days · Teen Families
Litchfield Hills (North/South), Connecticut
Waterfalls, Ridgelines & Village Greens: 2 Days in the Litchfield Hills
4 stops
2 Days · Solo
Gold Coast (Greenwich area), Connecticut
Salt Air & Storefronts: Two Days on Greenwich's Gold Coast
4 stops
2 Days · Solo
Quiet Corner (North/East), Connecticut
Stone, Brook, and Solitude: Two Days in Connecticut's Quiet Corner
3 stops
2 Days · Teen Families
Quiet Corner (North/East), Connecticut
Stone, Stream, and Woodland Legend: 2 Days in Connecticut's Quiet Corner
5 stops
2 Days · Teen Families
Gold Coast (Greenwich area), Connecticut
Salt Air & Sidewalk Cafés: 2 Days on Greenwich's Gold Coast
4 stops
2 Days · Active Retirees
New Haven, Connecticut
Ivy, Green, and Gaslight: Two Autumn Days in New Haven
4 stops
3 Days · Teen Families
Litchfield Hills (North/South), Connecticut
Green, Falls & Forest: 3 Days in the Litchfield Hills
5 stops
3 Days · Solo
Quiet Corner (North/East), Connecticut
Stone, Stream, and Solitude: 3 Days in Connecticut's Quiet Corner
8 stops
3 Days · Solo
New Haven, Connecticut
Ivy, Green, and Coal-Fired Pie: 3 Days Alone in New Haven
6 stops
3 Days · Teen Families
Hartford area, Connecticut
Ink, Atoms & the River: 3 Days in Hartford with Teens
8 stops
2 Days · Active Retirees
Quiet Corner (North/East), Connecticut
Stone, Stream, and Sugar Maples: Two Slow Days in the Quiet Corner
3 stops
3 Days · Solo
Litchfield Hills (North/South), Connecticut
Green Light, Falling Water: 3 Days Solo in the Litchfield Hills
6 stops
3 Days · Teen Families
Quiet Corner (North/East), Connecticut
Stone, Stream, and Story: A Quiet Corner Weekend for Wandering Families
4 stops
3 Days · Solo
Hartford area, Connecticut
Rivers, Rooms, and Written Words: 3 Days in Hartford
10 stops
2 Days · Active Retirees
Hartford area, Connecticut
Gilded Pages & River Light: Two Unhurried Days in Hartford
5 stops
3 Days · Teen Families
New Haven, Connecticut
Green Light & Gothic Towers: 3 Days in New Haven
8 stops
2 Days · Active Retirees
Litchfield Hills (North/South), Connecticut
Green Steeples & Cascading Water: Two Slow Days in Litchfield Hills
4 stops
3 Days · Solo
Hartford area, Connecticut
Ink, Iron, and River Light: 3 Days Alone in Hartford
8 stops
3 Days · Solo
New Haven, Connecticut
Ivy, Apizza & Amistad: 3 Days Alone in New Haven
8 stops
3 Days · Teen Families
Hartford area, Connecticut
Currents & Curiosities: A Family Weekend in Hartford
8 stops
3 Days · Teen Families
Quiet Corner (North/East), Connecticut
Stone, Brook & Legend: Three Days in Connecticut's Quiet Corner
6 stops
3 Days · Teen Families
New Haven, Connecticut
Ivy, Bones, and Brick: 3 Days in New Haven with Your Teens
8 stops
2 Days · Young Families
Quiet Corner (North/East), Connecticut
Stone, Stream, and Wolf Den: Two Slow Days in the Quiet Corner
3 stops
2 Days · Couples
Hartford area, Connecticut
River Light & Gilded Pages: Two Days in Hartford
7 stops
2 Days · Young Families
New Haven, Connecticut
Dinosaurs, Green Grass & Gothic Towers: A Family Weekend in New Haven
4 stops
2 Days · Couples
New Haven, Connecticut
Ivy, Elegy & Coal-Fired Pie: Two Days in New Haven
4 stops
2 Days · Young Families
Hartford area, Connecticut
Curiosity, Carousels & Twain's Gables: A Family Weekend in Hartford
4 stops
2 Days · Couples
Quiet Corner (North/East), Connecticut
Stone, Stream, and Hemlock Shadow: A Quiet Corner Escape for Two
4 stops
3 Days · Active Retirees
New Haven, Connecticut
Ivy, Ink, and Apizza: A Gentle 3 Days in New Haven
6 stops
2 Days · Young Families
Hartford area, Connecticut
Carousel Mornings & Curious Minds: A Family Weekend in Hartford
4 stops
2 Days · Couples
Quiet Corner (North/East), Connecticut
Stone, Stream, and Hemlock Shadow: Two Days in the Quiet Corner
3 stops
2 Days · Young Families
Quiet Corner (North/East), Connecticut
Stone Legends & Streamside Wandering: 2 Days in the Quiet Corner
4 stops
2 Days · Couples
New Haven, Connecticut
Ivy, Amber Light, and Coal-Fired Pie: Two Days in New Haven
5 stops
2 Days · Couples
Hartford area, Connecticut
Gaslight and River Light: A Hartford Weekend for Two
5 stops
2 Days · Young Families
New Haven, Connecticut
Dinosaurs, Green Grass & Golden Leaves: A Family Weekend in New Haven
3 stops
3 Days · Active Retirees
Quiet Corner (North/East), Connecticut
Stone, Stream, and Slow Light: 3 Days in the Quiet Corner
5 stops
3 Days · Active Retirees
Hartford area, Connecticut
Gilded Pages & River Light: Three Unhurried Days in Hartford
7 stops
3 Days · Couples
Quiet Corner (North/East), Connecticut
Stone, Brook, and Hemlock Shadow: Three Days in Connecticut's Quiet Corner
4 stops
3 Days · Couples
New Haven, Connecticut
Ivy, Green Light & Coal-Fired Nights: 3 Days in New Haven
6 stops
3 Days · Young Families
New Haven, Connecticut
Dinosaurs, Green Grass & Coal-Fired Pies: 3 Days in New Haven with Kids
4 stops
3 Days · Couples
Hartford area, Connecticut
Gilded Pages & River Light: A Couple's Weekend in Hartford
8 stops
3 Days · Young Families
Hartford area, Connecticut
Riverlight & Storybook Streets: 3 Days in Hartford with Little Ones
6 stops
3 Days · Teen Families
Gold Coast (Greenwich area), Connecticut
Salt Air & Sidewalk Chic: 3 Days on Greenwich's Gold Coast
6 stops
3 Days · Solo
Gold Coast (Greenwich area), Connecticut
Salt Air & Sidewalk Cafés: A Solo Escape to Greenwich's Gold Coast
6 stops
2 Days · Active Retirees
Gold Coast (Greenwich area), Connecticut
Salt Air & Storefronts: Two Slow Days on the Gold Coast
4 stops
3 Days · Solo
Litchfield Hills (North/South), Connecticut
Frost, Falls & Forest Quiet: 3 Solo Days in the Litchfield Hills
6 stops
3 Days · Teen Families
Litchfield Hills (North/South), Connecticut
Frost, Falls & Forest: A Winter Family Weekend in Litchfield Hills
6 stops
3 Days · Solo
Gold Coast (Greenwich area), Connecticut
Salt Air & Village Light: 3 Days Solo on Greenwich's Gold Coast
6 stops
2 Days · Active Retirees
Litchfield Hills (North/South), Connecticut
Village Greens & Winter Woods: Two Unhurried Days in the Litchfield Hills
3 stops
2 Days · Active Retirees
Gold Coast (Greenwich area), Connecticut
Salt Air & Storefronts: Two Slow Days on Greenwich's Gold Coast
4 stops
3 Days · Teen Families
Gold Coast (Greenwich area), Connecticut
Salt Air & Sidewalk Sundaes: 3 Days on Greenwich's Gold Coast
6 stops
2 Days · Young Families
Litchfield Hills (North/South), Connecticut
Green Grass & Waterfall Wonder: 2 Days in Litchfield Hills with Kids
4 stops
3 Days · Active Retirees
Litchfield Hills (North/South), Connecticut
Green Steeples & Quiet Cascades: 3 Days in the Litchfield Hills
7 stops
2 Days · Young Families
Gold Coast (Greenwich area), Connecticut
Sand Buckets & Salt Air: A Gentle Gold Coast Weekend
4 stops
2 Days · Couples
Gold Coast (Greenwich area), Connecticut
Salt Air & Sunset Grace: Two Days on Greenwich's Gold Coast
4 stops
2 Days · Young Families
Litchfield Hills (North/South), Connecticut
Snow-Quiet Villages: A Gentle Winter Weekend in Litchfield Hills
4 stops
3 Days · Active Retirees
Litchfield Hills (North/South), Connecticut
Slow Hills, Soft Light: 3 Winter Days in Litchfield Hills
6 stops
Showing 60 of 90 — explore all of Connecticut.
Connecticut's diverse regions offer curated weekend getaways for every traveler. This hub features 15 carefully crafted itineraries across six distinct destinations: Hartford, New Haven, the Quiet Corner, Greenwich's Gold Coast, the Litchfield Hills, and Mystic Country. Whether seeking romantic escapes, family adventures, or peaceful retreats, visitors will find multi-day itineraries tailored to their interests. From cultural landmarks and historic architecture to natural landscapes and waterfront charm, Connecticut's weekend destinations blend relaxation with discovery. Browse itineraries by region and duration to plan your next escape.
Frequently Asked Questions
What regions are covered in this Connecticut getaway guide?
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The guide features six destinations: Hartford, New Haven, the Quiet Corner (North and East), Greenwich's Gold Coast, the Litchfield Hills (North and South), and Mystic Country. Each region offers distinct character and attractions for weekend exploration.
How many itineraries are available to choose from?
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There are 15 itineraries available, ranging from 2-day to 3-day trips. Options include family-focused journeys, romantic escapes, and solitude-seeking adventures across Connecticut's varied regions.
Can I find itineraries for specific interests like families or couples?
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Yes. The collection includes itineraries designed for families, such as 'Green Grass, Big Bones & Small Steps: 3 Days in New Haven with Kids,' and romantic getaways like 'Ivy, Green & Golden Hour: Three Days of New Haven Romance' and 'Ink, Ivy & River Light: A Hartford Weekend for Two.'
What types of experiences can I expect on these getaways?
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Itineraries feature diverse experiences including cultural and architectural exploration, river and waterfront settings, natural landscapes, wildlife and forests, historic sites, and leisurely paced journeys through scenic areas.
More Collections
Or browse every Connecticut destination.