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 (45 minutes) to our Appalachian Trail start. This shorter hiking day is intended to get those muscles ready for more movement throughout the week. We will begin at the southernmost of the three New York and Connecticut border crossings and hike 4.2 miles up and along the Housatonic River and past Bull’s Bridge. This covered wooden bridge dates from the 19th century and is still in use today for car and foot traffic. From here there are several great views of the river, its dam and a cascading waterfall. We will end this section of our hike today at Schaghticoke Road and take a break for the first of many delicious picnic lunches shared together. We will then pick back up on the Appalachian Trail and tackle a short but challenging 1.9 mile section between Skiff Mountain Rd and River Rd. This hike will take us up and over the rocky summit of Caleb’s Peak via St John’s Ledges where we will enjoy gorgeous views of the Housatonic River valley and the town of Kent below. After we are done hiking for the day, we will travel back to our beautiful lodging to relax and unwind and enjoy a home cooked meal prepared by our talented guide/chefs! ( (B, L, D)

Distance: 6.1 miles

Total Elevation Gain: 1,291 feet

Total Elevation Loss: 1,712 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. We will head back to where we left off our morning hike yesterday, putting in at Schaghticoke Road and starting the day hiking north with a climb up Schaghticoke Mountain. We continue with more ups and downs over Chapel Pond Hill and Mt Algo then descending down to Macedonia Road. The bridge over Macedonia Brook is out so we will take a detour around and steeply climb up past the colorful Numeral Rock which is painted each year by the graduating class of the nearby boarding school. The trail today offers great views of the beautiful Housatonic River Valley and meanders across rocky slabs and over babbling brooks with plenty of places to dip your toes in the water! A challenging day, hiking 10.7 miles with just under 3,000 feet elevation, today's hike will take around 8 hours. We return again to the elegant and historic Pine Mansion to rest up and prepare for another big day tomorrow. (B, L, D) Distance: 10.7 miles

Total Elevation Gain: 2,781 feet

Total Elevation Loss: 2,424 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! Our day starts from River Rd with a lovely 4.5 mile flat walk along the banks of the Housatonic River and through large grassy meadows and farmland passing the Stewart Hollow Brook shelter. The river’s name is derived from the Mohican phrase “usi-a-di-en-uk” translated as “river of the Mountain Place”. We then ascend steeply from the river valley up over Silver Hill and continue with more ups and downs over and around Breadloaf Mountain and Pine Knob. More great views are to be had of the Housatonic River valley and the village of Cornwall Bridge. Today’s hike will take around 8 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: 11.3 miles

Total Elevation Gain: 2,219 feet

Total Elevation Loss: 1,778 feet

Overnight: Pine Plains, NY

After a healthy and delicious breakfast, we will hop in the van and set off for our next hike. We are a little over halfway through our Appalachian Adventure! We will begin where we left off yesterday at West Cornwall Road and hike 10.5 miles through Connecticut’s beautiful forest, passing by many streams along the way. We will stop for lunch, perhaps at Hanglider View where we can keep an eye out for turkey vultures and chicken hawks that are riding the thermals in the valley. We will continue on as we appreciate the beauty of our natural world and mindfully bathe in the forest while we walk. Our hike will end today at Great Falls Parking. At the end of the day we will enjoy a delicious meal seated next to your hiking comrades. (B, L, D)

Distance: 10.5 miles

Total Elevation Gain: 1,284 feet

Total Elevation Loss: 1, 254 feet

Overnight: Pine Plains, NY
After breakfast at the lodging, we’ll head to the trailhead and enjoy a mellow day of hiking along a ridgewalk with fantastic views of the surrounding countryside. During today’s 6.8 mile 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.” After our hike, we will visit 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! We will then return to our lodging to rest up before our last day of hiking, where we will complete the Connecticut section of the Appalachian trail. (B, L, D)

Distance: 6.8 miles

Total Elevation Gain: 1,284 feet

Total Elevation Loss: 1,254 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 Mt. Washington 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: 6.6 miles

Total Elevation Gain: 2,091 feet

Total Elevation Loss: 936 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.