Mount Mansfield Summit

Saturday, September 5

Hike to Vermont’s highest peak and celebrate the summit by the campfire.

Departure Location: Upper West Side

Sea Kayaking & Sandbar Barbecue

Saturday, September 5

Kayaking with Barbecue

Departure: Upper West Side

3500 Series: Sugarloaf Mountain

Saturday, September 5 - SOLD OUT

No. 13, Elevation: 3,810 feet

Departure Location: Upper West Side

Whitewater Rafting

Saturday, September 5

A fun day of rafting Class I-III Rapids

Departure Location: Union Square

Guides’ Choice Weekend: Devil’s Path

Saturday, September 5 - SOLD OUT

Test your limits on what many claim to be the toughest hiking path in the eastern United States.

Departure Location: Upper West Side

Whitewater Rafting

Sunday, September 6

A fun day of rafting Class I-III Rapids

Departure Location: Upper West Side

Millbrook Mountain & Lake Minnewaska

Sunday, September 6

Gemlike Lake Minnewaska to Millbrook Mountain; beautiful foliage and sweeping views!

Departure Location: Upper West Side

Hike with Adoptable Hounds

Sunday, September 6 - SOLD OUT

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Horseback Riding & Wine Tasting

Sunday, September 6

Ride through forest and fields. Sample wines and ciders

Departure Location: Upper West Side

Hike & Hound Pine Meadow

Monday, September 7

Assuage your “I live in the City and have a dog” guilt and get some healthful outdoor exercise with your best friend!

Surprise Lake Hike

Monday, September 7

A stunning day hike.

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, September 7

Experience Africa in a meaningful way

Awosting Falls

Monday, September 7

Moderate nine-mile hike to idyllic waterfalls

Departure Location: Union Square

3500 Series: Hunter Mountain

Saturday, September 12

No. 2, Elevation: 4,046 feet

Departure Location: Upper West Side

Hike & Howl

Saturday, September 12

Explore a wolf sanctuary then hike on the Kittatinny Ridge

Departure Location: Union Square

Black Rock Forest

Saturday, September 12

Visit forest lakes and enjoy gorgeous views

Departure Location: Union Square

Hike & Wine Tasting

Saturday, September 12

Stunning Views and New York Wine to Taste

Departure Location: Upper West Side

Storm King Hike & Sculpture Park

Saturday, September 12

Spring Hike and Storm King Tour

Departure Location: Upper West Side

Dog, Beach & Vine

Sunday, September 13

Bring your dog to this beach day and wine tour

Departure Location: Union Square

Guides’ Choice Hike: Blauvelt Mountain

Sunday, September 13

An aggressive pace, ambitious distance and challenging terrain distinguishes this hike as a Guides’ Choice.

Departure Location: Upper West Side

Schunemunk Mountain Hike

Sunday, September 13

Unique Rock Formations and Scenic Views

Departure Location: Upper West Side

Ship Rock Ridge Hike

Sunday, September 13

Departure Location: Union Square

Monastery & Meditation Hike

Sunday, September 13

A day of focus and inner peace.

Departure Location: Upper West Side

Adventure Fit

Monday, September 14

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

3500 Series: Giant Ledge & Panther Mountain

Saturday, September 19

No. 17, Elevation: 3,725 feet

Departure Location: Upper West Side

Hike & Brewery Tour

Saturday, September 19

Hiking and a pint

Departure Location: Union Square

Hike & Yoga

Saturday, September 19

Hike, stretch, restore…the perfect outdoor fitness combination of hiking and yoga.

Departure Location: Upper West Side

Awosting Falls

Saturday, September 19

Moderate nine-mile hike to idyllic waterfalls

Departure Location: Union Square

Raven Rocks and the Leatherman's Cave

Saturday, September 19

A relaxing hike in the shadow of massive rock formations

Departure Location: Union Square

Hudson River Sea Kayaking to Abandoned Castle

Sunday, September 20

Explore an abandoned castle on the Hudson.

Departure Location: Upper West Side

Photography Outing

Sunday, September 20

Learn how to really use that camera to capture the natural world around you.

Rock Climbing

Sunday, September 20

Rock Climb the legendary Shawangunk Ridge. No experience necessary.

Departure Location: Upper West Side

Tom Jones Mountain Hike

Sunday, September 20

Great views from the heart of Harriman State Park

Departure Location: Upper West Side

Horseback Riding & Wine Tasting

Sunday, September 20

Ride through forest and fields. Sample wines and ciders

Departure Location: Upper West Side

Hike High Point Mountain

Sunday, September 20

Gorgeous trail, sweeping views and a variety of terrain.

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, September 21

Experience Africa in a meaningful way

Adventure Fit

Monday, September 21

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

3500 Series: Indian Head Mountain

Saturday, September 26

No. 30, Elevation: 3,573 feet

Departure Location: Upper West Side

Bear Mountain Connecticut

Saturday, September 26

Wind through quaint, historic villages before beginning this hike to Connecticut’s highest peak.

Departure Location: Upper West Side

Hike & Whiskey Tasting

Saturday, September 26

Hike first…whiskey after! Breathtaking views at the legendary Shawangunk Mountains. Afterward, a tasting at NY State’s only whiskey distillery open to the public.

Departure Location: Union Square

Hike, Apple & Pumpkin Picking

Saturday, September 26

Fall Foliage Hike and Harvest

Departure Location: Union Square

Fall Foliage Rappelling

Saturday, September 26

Adrenaline-filled day with treetop views of fall foliage

Departure Location: Upper West Side

Dog, Beach & Vine

Saturday, September 26

Bring your dog to this beach day and wine tour

Departure Location: Union Square

Kaaterskill Falls Hike

Sunday, September 27

Gorgeous eight miles, sweeping views and a variety of terrain, including famous Kaaterskill Falls.

Departure Location: Upper West Side

Hike & Hound Pine Meadow

Sunday, September 27

Assuage your “I live in the City and have a dog” guilt and get some healthful outdoor exercise with your best friend!

Buck Mountain

Sunday, September 27

Beautiful hike with two secluded lakes

Departure Location: Union Square

Guide's Choice: Shawangunk Ridge Trail

Sunday, September 27

Bask in some of NY’s greatest views over 12 challenging miles

Departure Location: Upper West Side

Adventure Fit

Monday, September 28

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

3500 Series: Slide Mountain

Saturday, October 3

No. 1, Elevation: 4,182 feet

Departure Location: Upper West Side

Hike & Wine Tasting

Saturday, October 3

Stunning Views and New York Wine to Taste

Departure Location: Upper West Side

Monastery & Meditation Hike

Saturday, October 3

A day of focus and inner peace.

Departure Location: Upper West Side

Zipline & High Ropes Challenge Course

Saturday, October 3

An aerial forest adventure

Departure Location: Upper West Side (76th and Broadway, in front of Eastern Mountain Sports)

Raccoon Brook Hike

Saturday, October 3

A moderately challenging hike through diverse terrain and scenery with breathtaking views.

Departure Location: Upper West Side

Night Hike

Saturday, October 3

Hike beneath the night sky and toast marshmallows by the bonfire.

Departure Location: Upper West Side

Hike, Apple & Pumpkin Picking

Sunday, October 4

Fall Foliage Hike and Harvest

Departure Location: Union Square

Horseback Riding & Wine Tasting

Sunday, October 4

Ride through forest and fields. Sample wines and ciders

Departure Location: Union Square

Gertrude's Nose Hike in Minnewaska

Sunday, October 4

Spectacular views in Minnewaska State Park

Departure Location: Upper West Side

Rock Climbing

Sunday, October 4

Rock Climb the legendary Shawangunk Ridge. No experience necessary.

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, October 5

Experience Africa in a meaningful way

Adventure Fit

Monday, October 5

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

3500 Series: Peekamoose & Table Mountains

Saturday, October 10

No. 10 & 11, Elevation: 3,843 and 3,847 feet

Departure Location: Upper West Side

Hike, Apple & Pumpkin Picking

Saturday, October 10

Fall Foliage Hike and Harvest

Departure Location: Union Square

Dog, Beach & Vine

Saturday, October 10

Bring your dog to this beach day and wine tour

Departure Location: Union Square

Sunfish Pond Hike

Saturday, October 10

Explore the Kittatinny Mountains and forever change the way you think of New Jersey.

Departure Location: Union Square

Halloween Hike & Haunt in Sleepy Hollow

Saturday, October 10

Tricking and treating is always more fun on the trails. Join us on this ghoulish hike in legendary Sleepy Hollow.

Tandem Hang Gliding

Sunday, October 11

Feel the rush of flying!

Departure Location: Union Square

Hike & Howl

Sunday, October 11

Explore a wolf sanctuary then hike on the Kittatinny Ridge

Departure Location: Union Square

Hike & Whiskey Tasting

Sunday, October 11

Hike first…whiskey after! Breathtaking views at the legendary Shawangunk Mountains. Afterward, a tasting at NY State’s only whiskey distillery open to the public.

Departure Location: Union Square

Fall Foliage Rappelling

Sunday, October 11

Adrenaline-filled day with treetop views of fall foliage

Departure Location: Upper West Side

Surprise Lake Hike

Sunday, October 11

A stunning day hike.

Departure Location: Upper West Side

Fourteen Peaks Hike

Sunday, October 11

Fantastic twelve-mile challenging ascent of 14 peaks.

Departure Location: Upper West Side

Great preparation for Guide’s Choice hikes

Adventure Fit

Monday, October 12

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

3500 Series: Kaaterskill High Peak

Saturday, October 17

No. 23, Elevation: 3,655 feet

Departure Location: Upper West Side

Hike & Brewery Tour

Saturday, October 17

Hiking and a pint

Departure Location: Union Square

Russian Bear Hike

Saturday, October 17

Hike Harriman State Park to see the panoramic view from the “Russian Bear” boulder.

Departure Location: Upper West Side

Monastery & Meditation Hike

Saturday, October 17

A day of focus and inner peace.

Departure Location: Upper West Side

Horseback Riding & Wine Tasting

Saturday, October 17

Ride through forest and fields. Sample wines and ciders

Departure Location: Union Square

Halloween Hike & Haunt in Sleepy Hollow

Saturday, October 17

Tricking and treating is always more fun on the trails. Join us on this ghoulish hike in legendary Sleepy Hollow.

Hike & Hound Pine Meadow

Sunday, October 18

Assuage your “I live in the City and have a dog” guilt and get some healthful outdoor exercise with your best friend!

Hike, Apple & Pumpkin Picking

Sunday, October 18

Fall Foliage Hike and Harvest

Departure Location: Union Square

Storm King Hike & Sculpture Park

Sunday, October 18

Spring Hike and Storm King Tour

Departure Location: Upper West Side

Diamond Mountain Hike

Sunday, October 18

Gorgeous, moderate six-mile hike in Harriman State Park

Departure Location: Union Square

Schunemunk Mountain Hike

Sunday, October 18

Unique Rock Formations and Scenic Views

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, October 19

Experience Africa in a meaningful way

Adventure Fit

Monday, October 19

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

3500 Series: The Blackhead Range

Saturday, October 24

No. 3, 4 and 5, Elevations: 3,980 ft, 3,940 ft and 3,940 ft. 

No. 23, Elevation: 3,655 feet

Guide's Choice: Shawangunk Ridge Trail

Saturday, October 24

Bask in some of NY’s greatest views over 12 challenging miles

Departure Location: Upper West Side

Fall Foliage Rappelling

Saturday, October 24

Adrenaline-filled day with treetop views of fall foliage

Departure Location: Upper West Side

Halloween Hike & Haunt in Sleepy Hollow

Saturday, October 24 - SOLD OUT

Tricking and treating is always more fun on the trails. Join us on this ghoulish hike in legendary Sleepy Hollow.

Buck Mountain

Sunday, October 25

Beautiful hike with two secluded lakes

Departure Location: Union Square

Zipline & High Ropes Challenge Course

Sunday, October 25

An aerial forest adventure

Departure Location: Upper West Side (76th and Broadway, in front of Eastern Mountain Sports)

Rock Climbing

Sunday, October 25

Rock Climb the legendary Shawangunk Ridge. No experience necessary.

Departure Location: Upper West Side

Central Park Photography Class

Sunday, October 25

Learn to take amazing outdoor shots with your own camera

Adventure Fit

Monday, October 26

Discover Outdoors personal trainers take fitness outdoors for a full-body workout that will light all your senses on fire.

Hike & Howl

Saturday, October 31

Explore a wolf sanctuary then hike on the Kittatinny Ridge

Departure Location: Union Square

Hike & Whiskey Tasting

Saturday, October 31

Hike first…whiskey after! Breathtaking views at the legendary Shawangunk Mountains. Afterward, a tasting at NY State’s only whiskey distillery open to the public.

Departure Location: Union Square

Guides’ Choice Hike: Blauvelt Mountain

Saturday, October 31

An aggressive pace, ambitious distance and challenging terrain distinguishes this hike as a Guides’ Choice.

Departure Location: Upper West Side

Horseback Riding & Wine Tasting

Saturday, October 31

Ride through forest and fields. Sample wines and ciders

Departure Location: Upper West Side

Halloween Night Hike

Saturday, October 31

Hike beneath the night sky and share scary stories by the bonfire.

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, November 2

Experience Africa in a meaningful way