Slackpacking Connecticut

Destination: Kent, Connecticut

| Activities: Hiking and Slackpacking

This section of the Appalachian Trail features a well-maintained trail that winds through hardwood forests, over babbling brooks, and past long-range views of scenic valleys and cascading waterfalls. While this is a level 4 trip, the AT through Connecticut has features more forgiving terrain than most other sections of the trail leaving you with more energy to enjoy the other wonderful things Connecticut has to offer. On this trip, we’ll cover approximately 52 miles to complete the Connecticut section, returning at the end of the day to our elegant, historic lodging near Pine Plains, NY. While the terrain is less challenging than neighboring AT states, you'll still hike significant mileage on this trip -between 4.2 and 13.2 miles each day, which requires being in excellent physical condition. Maximum group size: 10


  • Completing the entire Connecticut section of the Appalachian Trail
  • Walking through beautiful and historic landscapes, and visiting quaint towns along the way
  • Climbing Bear Mountain, the tallest peak in Connecticut
  • Carrying only what you need for the day on your back
  • Exploring Connecticut's historic villages, enjoying a relaxing afternoon at Clover Brooke Farm and experiencing Kent Falls State Park
  • Returning to a comfortable bed and hot shower at the end of every day in our historic and elegant accommodations

Departures and Prices

June 23 to June 30, 2024
$3350.00 - FULL
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September 22 to September 29, 2024
$3350.00 - FULL
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  • 2-3 experienced AGC guides based on group size
  • Seven nights lodging
  • All meals from dinner on the first day through breakfast on the last day
  • All transportation within Connecticut and New York including round-trip transport between the Albany International Airport and our lodging, and daily shuttles to and from trailheads
  • Park entry fees
  • Not included: Transportation to Albany, alcoholic beverages, guide gratuities, and travel insurance.

Trip Documents

Trip Info

This trip is rated a level 4 on our fitness scale, as it involves hiking from 4 -13 miles a day on varied terrain (see itinerary for daily specific mileage). The Appalachian Trail is full of ups and downs; our biggest ascent on this trip is 3,000 feet over 13 miles. The trail will undoubtedly have rocks, exposed tree roots, and muddy sections. Slackpacking requires being in excellent physical condition with prior hiking experience. While we are unable to offer longer and shorter alternatives for each day of hiking, hikers are welcome to take a down day to stay behind and explore Pine Plains or relax in our lodging. To prepare for this trip, adding some specific conditioning such as strength training, endurance training, and longer aerobic workouts is recommended.Rating: 1 2 3 [4] 5.

While Connecticut does provide relatively well-graded terrain along the Appalachian Trail, hiking any part of the AT is a physical challenge that should not be taken lightly! The AT travels 50.1 miles through Connecticut, and on this slackpacking trip, we will hike all of them, completing this section in its entirety! Along the way, you will encounter rough and rocky trails, and some steep climbs and descents. Depending on weather, you may also navigate muddy trails and rocks and roots that will be slippery when wet. In Connecticut, the Appalachian Trail crosses over hills and valleys and through several towns in the Southern Taconic Range. To fully enjoy yourself on this trip, you should be comfortable hiking up to 13 miles a day for multiple days in a row.

We will be staying at the regal mansion in Pine Plains, NY. The Pines Mansion is elegant, historical, and you might even say magical. Each room is creatively decorated and takes you back into time. After hours of hiking you will find yourself ready to relax in your mansion with many, many amenities. The Pine Mansion includes a gourmet eat-in kitchen, butler's pantry, formal dining room, music room, library/game room, mud room, parlor, and 10 bedrooms. Here you will find a mix of shared rooms and single supplements.

Below is the proposed itinerary for the trip. As is true on any adventure travel trip, plans for any specific day may be modified due to weather considerations, unforeseen circumstances, new opportunities, and group interests.


Welcome to Slackpacking Connecticut! On this travel day, plan to fly into the Albany Airport (ALB) before 3PM, at which time our guides will meet you at baggage claim and shuttle you to our lodging. If you are driving, you can meet us at the Pine Plains Mansion at 4:30PM. We cannot wait to hike through northwest Connecticut with you! (D)
Overnight at Pine Plains, NY

Today is a warm-up day! We'll drive from Pine Plains to just south of Kent, Connecticut (~35 minutes) to our Appalachian Trail start. The short hiking day is intended to get those muscles ready for more movement throughout the week. Our 4.2 miles will lead us across the Housatonic River on the 19th century covered Bull Bridge and offer us many great views of the river, its dam, and a cascading waterfall. Today’s short hike will end at Schaghticoke road. From there, we will take a quick jaunt to Kent Falls State Park for the first of many delicious picnic lunches. We will then drive back to the lodging to prepare for our bucolic afternoon at Clover Brooke Farm. At this pastoral family owned Llama and Alpaca farm, we’ll have an opportunity to spend time with the adorable residents - cute goats and fluffy alpacas! Depending on availability, we may take part in goat yoga or try our hand in artisanal farm crafts; we will have to see what is in store for us all! (B, L, D)

Distance: 4.2miles

Total Elevation Gain: 882 feet

Total Elevation Loss: 1,411 feet

Overnight: Pine Plains, NY

Rise and shine! Time for a hearty home cooked breakfast provided by our AGC guides in preparation for the day. As with all of our slackpacking trips, we will start where we left off yesterday, putting in at Schaghticoke Road and hiking north with continued views of the Housatonic River Valley. This area will take you back in time with its historical heritage and rural charm. The trail here meanders across rocky slabs and over babbling brooks with plenty of places to dip your toes in the water! The hiking today will be about 7.7 miles, and will take around 4.5 hours. Time allowing, we will be able to explore the quaint town of Kent this afternoon. Tomorrow, we will continue to increase our daily mileage in preparation for the trail ahead. (B, L, D) Distance: 7.7 miles

Total Elevation Gain: 1,900 feet

Total Elevation Loss: 2,150 feet

Overnight: Pine Plains, NY

Did you know that it wasn't until 1929 that the Appalachian Trail in Connecticut was completed? Amazing to think that you are here now continuing to enjoy this epic adventure on the trail. After the first few days, you may now start to feel like you have your “trail legs” under you - and they should be well up to the challenge of today’s hike! On today's hike we will cross Macedonia Brook on a log footbridge, and enjoy long-range views of the town of Kent as we cross the rocky summit of Caleb’s Peak. Descending the St. John’s Ledges towards the end of the day will be a challenge, but the rocky outcropping faces east and provides gorgeous views of the river valley and St. John’s Peak. Today’s hike will take around 6 hours to complete. Once the hiking has come to an end we will head back to our comfy and cozy lodging to wind down for dinner time.(B,L,D)

Distance: 9.1 miles

Total Elevation Gain: 1,570 feet

Total Elevation Loss: 2,228 feet

Overnight: Pine Plains, NY

After a healthy and delicious breakfast, we’ll begin where we left off at Dawn Hill Road, and continue up to a series of ridges with fantastic views. Our first break spot will be a view at aptly named Pine Knob, a ledge with southward views to the village of Cornwall Bridge. The pine trees offer enough shade for a comfortable break. During the break, we can take a moment to appreciate the beauty of our natural world and mindfully bathe in the forest before continuing on. Keep an eye out - turkey vultures and chicken hawks often ride the thermals over this valley throughout the day, and swoop close to the overlook on occasion. We will hike past a series of streams and brooks before ending our day at West Cornwall Rd. At the end of the day we will enjoy a delicious meal seated next to your hiking comrades. (B, L, D)

Distance: 6.8 miles

Total Elevation Gain: 2,169 feet

Total Elevation Loss: 2,395 feet

Overnight: Pine Plains, NY
On this day, we will enjoy a mellow day of hiking along a ridge walk with fantastic views of the surrounding countryside. During today’s hike, we’ll summit Mount Easter and enjoy long-range views of the Southern Taconic Range from Hang Glider view. This unique sub-range of the Appalachian Mountains runs along the New York and Massachusetts border, and dips south into Connecticut, and north into Vermont. The name Taconic comes from an Algonquian word, from the Lenni Lenape, “Taghkanic” or “Taughannock". Loosely translated, it means “place in the woods” or “waterfall in the woods.” This is a very appropriate name for the place where we’ll end today’s hike, at the Warren Turnpike just outside Falls Village, CT: where you may hear a large waterfall rumbling in the distance. Don’t worry - we’ll walk through this quaint village tomorrow morning! Rest up, because tomorrow is our last, and longest day of hiking, where we’ll complete the Connecticut section of trail. (Optional: If your body and soul is calling for a massage at the end of the day you could check out the local massage therapist in Pine Plains). (B, L, D)

Distance: 10 miles

Total Elevation Gain: 1,661 feet

Total Elevation Loss: 1,708 feet

Overnight: Pine Plains, NY

Our last day of hiking has arrived! As usual, we will wake up, enjoy a hearty breakfast, and begin hiking where we last left off. Today is a special day: we will cross the border into Massachusetts, and complete the entire Connecticut section of the Appalachian Trail, while enjoying more amazing viewpoints along the way. We’ll begin in Falls Village, a quaint town with an iron bridge we will cross as we hike along the AT. Keep your eye out for Great Falls, a nearby dam with a large cascade at an old iron works site. This site was essential for early settlers, where the high water volume powered grist, bolting, fulling and paper mills, and the area’s famous ironworks. As we walk along the AT today, we will climb Lion’s Head for views, and summit Bear Mountain, which is the highest peak in Connecticut. We will then take a short spur trail to the just south of Paradise Lane Trail. We will walk along this spur trail .5 miles to Riga auto road for shuttle pickup. This evening we will celebrate all of our week's achievements with a dinner out on the town!(B, L, D)

Distance: 13.2 miles

Total Elevation Gain: 3,354 feet

Total Elevation Loss: 492 feet

Overnight: Pine Plains, NY
Congratulations, you have completed the Slackpacking Connecticut trip! After a week of exploration and hiking, the final day has arrived. Can you believe it? You have hiked the Connecticut portion of the Appalachian Trail. Give yourself a pat on the back! On this final day, we will enjoy breakfast together and then a group shuttle with a guide will head to the airport around 9AM. (B)

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  1. Where do we eat?

    The guides will be cooking breakfasts and most dinners at the vacation home. Before you leave in the morning the guides will put out lunch options and you will prepare a packed lunch. You'll go out for one dinner where you can order off the menu; other nights you'll relax in the vacation home and have dinner there.
  2. What dietary preferences or restrictions can you accommodate on this trip?

    If we know well in advance, we can accommodate vegetarian, lactose-free, and gluten-sensitive diets. We cannot guarantee a completely gluten-free diet and we cannot provide a kitchen guaranteed to be free of cross-contamination. If you are vegan, we ask that you bring some additional protein bars; and if you are gluten-sensitive, please bring some gluten-free snacks. If you have severe allergies, Celiac disease and/or other significant dietary restrictions, please call the office before you register.