Valentine's Day Snowshoe & Wine Tasting

Saturday, February 14

Bring your sweetheart or meet your match on the trails on this perfect winter’s day.

Departure Location: Union Square

Wilderness First Responder Certification

Friday, February 27 - SOLD OUT

As part of our continued pursuit of education, Discover Outdoors is very proud to sponsor the most widely recognized and most often required outdoor leader certification, the Wilderness First Responder course. This industry standard certification is rarely offered in New York City.

Ice Climbing

Saturday, March 7

Learn to scale frozen waterfalls in this climbing clinic and adventure.

Departure Location: Upper West Side

3500 Series: Slide Mountain

Saturday, March 7

No. 1, Elevation: 4,182 feet

Snowshoes provided.

Winter Horseback Ride & Wine Tasting

Sunday, March 8

Ride through frost-touched forests before you sample wines and ciders to the tunes of live music.

Departure Location: Upper West Side

Snowshoe Diamond Mountain

Sunday, March 8

Learn to snowshoe in a day on this scenic trail in Harriman State Park.

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, March 9

Experience Africa in a meaningful way

FREE Kilimanjaro Information Session

Tuesday, March 10

Take a tour of Mount Kilimanjaro

Bear Mountain Summit

Saturday, March 14

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

Departure Location: Upper West Side

3500 Series: Peekamoose & Table Mountains

Saturday, March 14

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

Snowshoes provided.

St. Patrick’s Snowshoe & Brew

Saturday, March 14

This year, earn your St. Patty’s celebration with an epic day on the wintry trails.

Departure Location: Union Square

Snowshoe Canopus Lake

Sunday, March 15

This winter, you are invited to join us for a snowshoe adventure along the famed Appalachian Trail.

Departure Location: Upper West Side

Snowshoe Hike & Whiskey Tasting

Sunday, March 15

Leave the treadmill behind and get the ultimate winter workout amid the breathtaking views of the legendary Shawangunk Mountains.

Departure Location: Union Square

Snowshoe & Howl

Sunday, March 15

Snowshoe on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Sunday, March 15

The don’t-miss winter one-two punch is back and better than ever.

Departure Location: Upper West Side

Winter Horseback Ride & Wine Tasting

Saturday, March 21

Ride through frost-touched forests before you sample wines and ciders to the tunes of live music.

Departure Location: Union Square

3500 Series: Kaaterskill High Peak

Saturday, March 21

No. 23, Elevation: 3,655 feet

Snowshoes provided.

Hike with Adoptable Hounds

Saturday, March 21

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Snowshoe & Brew

Sunday, March 22

Snowshoes and a pint

Departure Location: Union Square

Ice Climbing

Sunday, March 22

Learn to scale frozen waterfalls in this climbing clinic and adventure.

Departure Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Sunday, March 22

The don’t-miss winter one-two punch is back and better than ever.

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, March 23

Experience Africa in a meaningful way

Snowshoe & Wine Tasting

Saturday, March 28 - SOLD OUT

Learn to snow shoe and explore a winter wonderland before reaping the rewards at one of New York’s finest wineries.

Departure Location: Union Square

3500 Series: The Blackhead Range

Saturday, March 28

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

Departure Location: Upper West Side

Hike with Adoptable Hounds

Saturday, March 28

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Winter Horseback Ride & Wine Tasting

Sunday, March 29

Ride through frost-touched forests before you sample wines and ciders to the tunes of live music.

Departure Location: Upper West Side

Storm King Mountain

Sunday, March 29

Sweeping views of the Hudson River and Valley

Departure Location: Union Square

Mohonk Scramble & Table Rocks Hike

Sunday, March 29

Stunning odyssey in the Shawangunks: challenging scramble plus six miles of gorgeous hiking.

Includes park entrance fee.

Hike & Howl

Saturday, April 4

Hike on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Penn Station

3500 Series: Plateau Mountain

Saturday, April 4

No. 12, Elevation: 3,856

Departure Location: Upper West Side

Easter Hike & Scavenger Hunt

Saturday, April 4

A beautiful, easy-to-moderate hike with a little hippity, hoppity fun for the season.

Night Hike

Saturday, April 4

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

Departure Location: Penn Station Area

Clydesdale Horseback Ride & Brewery

Sunday, April 5

Ride majestic clydesdales through the countryside.

Departure Location: Union Square

Gertrude's Nose Hike in Minnewaska

Sunday, April 5

Spectacular views in Minnewaska State Park

Departure Location: Upper West Side

Monastery & Meditation Hike

Sunday, April 5

A day of focus and inner peace.

Departure Location: Upper West Side

Hike & Wine Tasting

Sunday, April 5

Stunning Views and New York Wine to Taste

Departure Location: Union Square

Africa Volunteer Trip Aiding Elephants

Monday, April 6

Experience Africa in a meaningful way

3500 Series: Wittenberg & Cornell Mountains

Saturday, April 11

No. 8 and 14, Elevation: 3,784 and 3,868 feet

Departure Location: Upper West Side

Hike Iron Mine & Lemon Squeezer

Saturday, April 11

Fascinating rock features along a beautiful trail

Departure Location: Union Square

Horseback Riding & Wine Tasting

Saturday, April 11

Ride through forest and fields. Sample wines and ciders

Departure Location: Union Square

Millbrook Mountain & Lake Minnewaska

Saturday, April 11

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

Departure Location: Upper West Side

Central Park Photography Class

Saturday, April 11

Learn to take amazing outdoor shots with your own camera

Rock Climbing

Sunday, April 12

Rock Climb the legendary Shawangunk Ridge. No experience necessary.

Departure Location: Upper West Side

Awosting Falls

Sunday, April 12

Moderate nine-mile hike to idyllic waterfalls

Departure Location: Union Square

Canopus Lake Hike

Sunday, April 12

Casual Hike on the Appalachian Trail

Departure Location: Upper West Side

Trek to Machu Picchu

Monday, April 13

Follow the footsteps of the Incas to Machu Picchu.

Brooklyn Bridge Greenway Sunset Photography

Thursday, April 16

Capture the Manhattan Skyline at Sunset

Hawk Mountain Hike and Wine Tasting

Saturday, April 18

Explore nature in raw form, with raptors high above and remnants of the ice age below us.

Departure Location: Union Square

Clydesdale Horseback Ride & Brewery

Saturday, April 18

Ride majestic clydesdales through the countryside.

Departure Location: Union Square

3500 Series: Sugarloaf Mountain

Saturday, April 18

No. 13, Elevation: 3,810 feet

Departure Location: Upper West Side

Hike & Brewery Tour

Saturday, April 18

Hiking and a pint

Departure Location: Union Square

Hike with Adoptable Hounds

Saturday, April 18

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Storm King Mountain

Sunday, April 19

Sweeping views of the Hudson River and Valley

Departure Location: Union Square

Kaaterskill Falls Hike

Sunday, April 19

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

Departure Location: Upper West Side

Hike & Hound Pine Meadow

Sunday, April 19

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

Hike & Howl

Sunday, April 19

Hike on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Penn Station

Buck Mountain

Sunday, April 19

Beautiful hike with two secluded lakes

Departure Location: Union Square

Africa Volunteer Trip Aiding Elephants

Monday, April 20

Experience Africa in a meaningful way

Beach Horseback Riding & Wine Tasting

Saturday, April 25

Ride the beaches on America’s oldest cattle ranch.

Departure Location: Union Square

Surprise Lake Hike

Saturday, April 25

A stunning day hike.

Departure Location: Upper West Side

Hike with Adoptable Hounds

Saturday, April 25

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Central Park Photography Class

Saturday, April 25

Learn to take amazing outdoor shots with your own camera

Dog, Beach & Vine

Sunday, April 26

Bring your dog to this beach day and wine tour

Departure Location: Union Square

Raccoon Brook Hike

Sunday, April 26

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

Departure Location: Upper West Side

Hike & Whiskey Tasting

Sunday, April 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

3500 Series: Giant Ledge & Panther Mountain

Saturday, May 2

No. 17, Elevation: 3,725 feet

Departure Location: Upper West Side

Hike & Brewery Tour

Saturday, May 2

Hiking and a pint

Departure Location: Union Square

Schunemunk Mountain Hike

Saturday, May 2

Unique Rock Formations and Scenic Views

Departure Location: Upper West Side

Awosting Falls

Saturday, May 2

Moderate nine-mile hike to idyllic waterfalls

Departure Location: Union Square

Hike with Adoptable Hounds

Saturday, May 2

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Zipline & High Ropes Challenge Course

Sunday, May 3

An aerial forest adventure

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

Hang Gliding

Sunday, May 3

Feel the rush of flying!

Departure Location: Upper West Side

Hike & Howl

Sunday, May 3

Hike on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Union Square

Hike, Swim, & Yoga

Sunday, May 3

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

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, May 4

Experience Africa in a meaningful way

Wilderness First Responder Recertification

Saturday, May 9

As part of our continued pursuit of education, Discover Outdoors is very proud to offer the opportunity to recertify your existing Wilderness First Responder Certification. This recertification is rarely offered in New York City.

Hike & Hound Pine Meadow

Saturday, May 9

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

3500 Series: Indian Head Mountain

Saturday, May 9

No. 30, Elevation: 3,573 feet

Departure Location: Upper West Side

Whitewater Rafting

Saturday, May 9

A fun day of rafting Class I-III Rapids

Departure Location: Upper West Side

Waterfall Canyoneering

Saturday, May 9

Adrenaline-filled day of canyoneering down multiple cascading waterfalls!

Departure Location: Penn Station

Night Hike

Saturday, May 9

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

Departure Location: Upper West Side

Central Park Photography Class

Saturday, May 9

Learn to take amazing outdoor shots with your own camera

Clydesdale Horseback Ride & Brewery

Sunday, May 10

Ride majestic clydesdales through the countryside.

Departure Location: Union Square

Hudson River Sea Kayaking to Abandoned Castle

Sunday, May 10

Explore an abandoned castle on the Hudson.

Departure Location: Upper West Side

Rock Climbing

Sunday, May 10

Rock Climb the legendary Shawangunk Ridge. No experience necessary.

Departure Location: Upper West Side

Beach Horseback Riding & Wine Tasting

Sunday, May 10

Ride the beaches on America’s oldest cattle ranch.

Departure Location: Union Square

Monastery & Meditation Hike

Sunday, May 10

A day of focus and inner peace.

Departure Location: Upper West Side

Photography Outing

Sunday, May 10

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

Storm King Mountain

Sunday, May 10

Sweeping views of the Hudson River and Valley

Departure Location: Union Square

3500 Series: Slide Mountain

Saturday, May 16

No. 1, Elevation: 4,182 feet

Departure Location: Upper West Side

Diamond Mountain Hike

Saturday, May 16

Gorgeous, moderate six-mile hike in Harriman State Park

Departure Location: Union Square

Whitewater Rafting

Saturday, May 16

A fun day of rafting Class I-III Rapids

Departure Location: Upper West Side

Hot Air Balloon Adventure

Saturday, May 16

Take to the skies for this aerial adventure of a lifetime.

Hike with Adoptable Hounds

Saturday, May 16

Hike with adoptable dogs.

A portion of the proceeds goes to Animal Haven.

Hike & Brewery Tour

Saturday, May 16

Hiking and a pint

Departure Location: Union Square

Fourteen Peaks Hike

Sunday, May 17

Fantastic twelve-mile challenging ascent of 14 peaks.

Departure Location: Upper West Side

Great preparation for Guide’s Choice hikes

Dog, Beach & Vine

Sunday, May 17

Bring your dog to this beach day and wine tour

Departure Location: Union Square

Hawk Mountain Hike and Wine Tasting

Sunday, May 17

Explore nature in raw form, with raptors high above and remnants of the ice age below us.

Departure Location: Union Square

Hike, Swim, & Yoga

Sunday, May 17

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

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, May 18

Experience Africa in a meaningful way