New York's Catskills Hiking & Kayaking – Lodge Based

Trip Length4 Days
Group Size4-12
Activity level
Starting from
$2,499for REI Members
$2,749 for non-members
DeparturesJun 2025-Sep 2025

Explore the hidden gems of the Catskills

Just a few hours north of the hustle and bustle of New York City , the Catskill Mountains offer a serene escape into nature's wild beauty. With their towering peaks, forested valleys, and clear mountain streams, the Catskills have long been a haven for artists, adventures, and anyone looking to escape into unspoiled wilderness. The Catskills boast a unique blend of rugged beauty and tranquil charm that invite exploration and true relaxation.

During this 4-day trip, we’ll explore the best of the Catskills by foot and kayak. We’ll hike through verdant forests to scenic overlooks, visit plunging waterfalls, and paddle on calm waters, immersing ourselves in the region’s hidden gems. By day, we’ll challenge ourselves in nature, and by night, we’ll relax in cozy accommodations reflecting on the day’s adventures. With our guides sharing local knowledge, every moment is enriched with the history and beauty of the Catskills.

Explore the hidden gems of the Catskills, one waterfall at a time.

Trip Highlights

  • Hike to the breathtaking 260’ Kaaterskill Falls
  • Explore charming and historic mountain towns in the Catskills
  • Enjoy a peaceful paddle on the Hudson River
  • Summit Hunter Mountain for 360-degree views of the Catskill Mountains, Hudson River Valley, the Berkshires, and the Taconics

Activities

This trip is rated Moderate [3]. Trip members should be capable of hiking up to 8 miles while carrying a daypack that weighs 10-15 pounds on trails with elevation gains/losses of up to 2,145'. Hiking trails are made up of varied terrain including several steep climbs, loose rock, and slippery roots. Beginning kayakers are welcome but participants must be able to swim and at ease in a small boat on the open water for 2-4 hours. To maximize your enjoyment of the trip and to avoid sore muscles, we suggest that you engage in a regular exercise regimen beginning at least three months prior to your departure. Most important to your overall enjoyment is your overall fitness level.

  • Kayaking
  • Hiking
  • Multisport

What's Included

Three nights of accommodations; All meals as noted in the daily itinerary; Professional Guide(s); All vehicle transfers as noted in the daily itinerary; All park entry & permit fees

Accommodations

Hotel, 2 nights; Cabin, 1 night

Your Adventure Itinerary

Itinerary map for New York's Catskills Hiking & Kayaking – Lodge Based
Day 1

Explore the town of Woodstock and hike Overlook Mountain

Our journey begins with a morning pickup in Newark before we drive north into the heart of the Catskills. Our first adventure takes us up the historic trail of Overlook Mountain, where a fire tower, old hotel ruins, and sweeping views of the Hudson River Valley and surrounding peaks greet us at the summit. After our hike, we’ll explore the vibrant town of Woodstock, famed for its artsy charm and connection to music history. In the evening, we transfer to Hunter, where we check in to our hotel and enjoy a hearty welcome dinner. Lunch and dinner included.

Hiking: 4.5 miles; Elevation gain/loss: 1,434’; Van transfer: 3 hours

Day 2

Summit Hunter Mountain

Today, we tackle Hunter Mountain, the second-highest peak in the Catskills and the toughest hike on our trip. Our ascent takes us through dense forests and steep sections, leading to the 4040’ summit where the Hunter Mountain Fire Tower awaits. At the top of the tower, we’re rewarded with 360’ breathtaking vistas that include the Catskill Mountains, the Berkshires, the Hudson River Valley, the Taconics, and sometimes (on a clear day) you can see the Manhattan skyline!  After our challenging hike, we return to Hunter for some well-deserved relaxation at our hotel. In the evening, we head to a local restaurant for dinner. All meals included.

Hiking: 8 miles; Elevation gain/loss: 2,138’/2,145’; Van transfer: 1 hour

Day 3

Hike to Kaaterskill Falls & Kayak at Susan’s Pleasant Pheasant Farm

Today we check out of our hotel and embark on a scenic hike to Kaaterskill Falls, the tallest two-tier waterfall in New York. We continue onto the Escarpment Loop, where panoramic views unfold before us. Afterward, we head to Susan's Pleasant Pheasant Farm for an afternoon of kayaking on the farm’s peaceful waters, with opportunities for hiking and swimming. In the late afternoon, we transfer to our home for our final night together, small, private cabins nestled in a serene forest of oak, spruce, and pine. After getting settled in, we’ll enjoy dinner at a nearby restaurant before returning to our cabins for a peaceful evening. All meals included.

Hiking: 4-6 miles; Elevation gain/loss: up to 1,531’/1536’; Kayaking: 1-2 hours; Van transfer: 2.5 hours

Day 4

Paddle the Hudson River and return to Newark

You’ll want to rise a little early this morning, but no need to get out of bed just yet. Watch a family of deer hunt for acorns just a few feet away from the warmth of your cozy bed. Just outside, your guide is preparing coffee and a delicious breakfast to fuel our final adventure together. After we pack up, we head to Athens for a scenic kayaking adventure on the Hudson River. After a couple of hours paddling along this historic waterway, we begin our drive to Newark, stopping for a celebratory farewell lunch along the way. We return to Newark late this afternoon and bid farewell. Breakfast and lunch included.

Kayaking: 2-3 hours; Van transfer: 2.5 hours

Itinerary map for New York's Catskills Hiking & Kayaking – Lodge Based

Trip specifics may change over time. Reviews reflect the version of the trip that was active at the time the reviewer took it. Please review the itinerary as described above and call our team for any additional details.