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Weekend Appalachian Trail Hike in Connecticut with Gabi
2 days
New York City, USA
About this activity
Join Gabi, content creator, local hiking enthusiast, and your trail guide, for a multiday hike along one of the most beautiful and manageable stretches of the Appalachian Trail,winding through the forested hills and river valleys of Northwest Connecticut.
Highlights
- 12–18 mile weekend hike
- Scenic views and forest trails
- Peaceful campsites under stars
- Wildlife spotting opportunities
- Led by experienced thru-hiker
Full description
This weekend Appalachian Trail hike in Connecticut is designed to balance challenge and accessibility, covering 12–18 miles of beautiful forest, ridges, and rivers. It’s perfect for beginners, first-timers, or hikers returning after time away. You’ll be guided by Gabi Cerra, an experienced through-hiker who has completed over 800 miles of the AT and brings humor, patience, and deep knowledge of the trail. Expect panoramic mountain views, peaceful campsites under the stars, glimpses of wildlife, supportive pacing, and practical navigation tips. Leave with new skills, confidence, and the satisfaction of experiencing one of America’s most iconic footpaths.
Itinerary
Day 1 (Morning):
Meet at the CT/NY border trailhead in Northwest Connecticut, at Hoyt Road in Sharon at 8am. Group briefing, gear check, stretch, and set out on the trail. Gentle introduction hike through shaded woodland and rolling hills (approx. 6-10 miles). Camp setup at a designated shelter or campsite. Trail dinner + hangout before settling in for the night.
Day 2 (Full Day Hike):
Early start with coffee and breakfast. Continue along the Appalachian Trail through scenic ridgelines and lush valleys. Gabi shares local insights, nature knowledge, and confidence tips for hiking solo or in small groups. Midday lunch + journaling/photo stop. Recap of skills learned. Return to pickup trailhead by evening.
This itinerary is flexible depending on group pace and comfort, it can be adjusted for a more relaxed or slightly faster adventure. Please arrange for pickup at the end point (will be discussed depending on pace/comfort level) or plan to pay a shuttle driver to bring you back to your car. A shuttle driver will need to be notified ahead of time with a day, and eta the day of. Gabi can provide options and contact info.
Meet at the CT/NY border trailhead in Northwest Connecticut, at Hoyt Road in Sharon at 8am. Group briefing, gear check, stretch, and set out on the trail. Gentle introduction hike through shaded woodland and rolling hills (approx. 6-10 miles). Camp setup at a designated shelter or campsite. Trail dinner + hangout before settling in for the night.
Day 2 (Full Day Hike):
Early start with coffee and breakfast. Continue along the Appalachian Trail through scenic ridgelines and lush valleys. Gabi shares local insights, nature knowledge, and confidence tips for hiking solo or in small groups. Midday lunch + journaling/photo stop. Recap of skills learned. Return to pickup trailhead by evening.
This itinerary is flexible depending on group pace and comfort, it can be adjusted for a more relaxed or slightly faster adventure. Please arrange for pickup at the end point (will be discussed depending on pace/comfort level) or plan to pay a shuttle driver to bring you back to your car. A shuttle driver will need to be notified ahead of time with a day, and eta the day of. Gabi can provide options and contact info.
Included / Excluded
- 2 day, 1 night guided hike on the CT section of the AT (mileage tailored to group comfort)
- Camp setup support and tips (BYO gear or let us know if you need help buying gear)
- Trail food + water filtering guidance
- Nature knowledge, navigation tips, and content-creation pointers if desired
- Packing checklist and prep call before the trip
- Meals and snacks
- Camping gear and equipment
- Personal travel insurance
- Transportation to trailhead
Meeting point
Start Location
Hoyt Road, Sharon Springs, NY, USA
Important information
Know before you book
- Hike covers 12–18 miles total
- Book at least 1 week in advance
- Refunds up to 15 days before
Know before you go
- Bring meals, snacks, and water bottle
- Pack your own camping gear
- Basic hiking fitness recommended
Cancellation policy
Free cancellation up to 24 hours before the activity starts
Full refund 15 days prior (minus processing fee)