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Hike & Howl

Saturday, December 20

Hike on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Union Square

Storm King Mountain

Sunday, December 21

Sweeping views of the Hudson River and Valley

Departure Location: Union Square

Adventure Fit

Monday, December 22

Train for your next adventure.

Snowshoe Minnewaska Preserve

Saturday, December 27

Bask in the serenity of winter on this snowshoeing trek through nature.

Departure Location: Upper West Side

Winter Horseback Ride & Wine Tasting

Sunday, December 28

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

Departure Location: Union Square

Adventure Fit

Monday, December 29

Train for your next adventure.

New Year's Eve White Mountains Getaway

Wednesday, December 31

Ring in the New Year with a winter adventure in New Hampshire’s White Mountains on this four day/three night long weekend of snowshoeing, igloo building, mountainside celebrations.

Pickup Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Thursday, January 1

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

Departure Location: Upper West Side

Guides' Choice: Snowshoe Slide Mountain

Thursday, January 1

Experience the Catskills like most never do as you snowshoe to the summit.

Departure Location: Upper West Side

Snowshoe Beautiful Buck Mountain

Saturday, January 3

Escape the city for a snowshoe among the Buck Mountain forest and visit two secluded lakes.

Departure Location: Union Square

Cross Country Ski & Snowshoe Trek

Saturday, January 3

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

Departure Location: Union Square

Winter Horseback Ride & Wine Tasting

Saturday, January 3

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

Departure Location: Upper West Side

Snowshoe & Howl

Sunday, January 4

Snowshoe on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Union Square

Snowshoe Hike & Whiskey Tasting

Sunday, January 4

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

Departure Location: Upper West Side

Kilimanjaro Information Session

Tuesday, January 6

Take a tour of Mount Kilimanjaro

Snowshoe Minnewaska Preserve

Saturday, January 10

Bask in the serenity of winter on this snowshoeing trek through nature.

Departure Location: Upper West Side

Ice Climbing

Saturday, January 10

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

Departure Location: Upper West Side

Snowshoe & Wine Tasting

Saturday, January 10

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

Cross Country Ski & Snowshoe Trek

Sunday, January 11

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, January 12

Experience Africa in a meaningful way

Adventure Fit for Team Allianz

Wednesday, January 14

Team up to get fit with Discover Outdoors.

Snowshoe Adventure at Canopus Lake

Saturday, January 17

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

Departure Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Saturday, January 17

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

Departure Location: Union Square

Winter Horseback Ride & Wine Tasting

Saturday, January 17

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

Departure Location: Union Square

Snowshoe & Hound

Sunday, January 18

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

Departure Locations: Union Square & Upper West Side

Snowshoe & Brew

Sunday, January 18

Snowshoes and a pint

Departure Location: Union Square

Guides' Choice: Snowshoe Blauvelt Mountain

Saturday, January 24

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

Departure Location: Union Square

Snowshoe & Howl

Saturday, January 24

Snowshoe on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Upper West Side

Snowshoe Safari and Scramble

Sunday, January 25

Prepare for the adventure of the winter on this challenging snowshoe trek through the Delaware Water Gap.

Cross Country Ski & Snowshoe Trek

Sunday, January 25

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

Departure Location: Upper West Side

Winter Horseback Ride & Wine Tasting

Sunday, January 25

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

Departure Location: Union Square

Africa Volunteer Trip Aiding Elephants

Monday, January 26

Experience Africa in a meaningful way

Ice Climbing

Saturday, January 31

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

Departure Location: Upper West Side

Snowshoe Minnewaska Preserve

Saturday, January 31

Bask in the serenity of winter on this snowshoeing trek through nature.

Departure Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Saturday, January 31

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

Departure Location: Union Square

Snowshoe & Hound

Sunday, February 1

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

Departure Locations: Union Square & Upper West Side

Snowshoe & Brew

Saturday, February 7

Snowshoes and a pint

Departure Location: Union Square

Snowshoe Hike & Whiskey Tasting

Saturday, February 7

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

Departure Location: Upper West Side

Ice Climbing

Sunday, February 8

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

Departure Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Sunday, February 8

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

Departure Location: Upper West Side

Winter Horseback Ride & Wine Tasting

Sunday, February 8

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

Departure Location: Upper West Side

Africa Volunteer Trip Aiding Elephants

Monday, February 9

Experience Africa in a meaningful way

Ice Climbing

Saturday, February 14

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

Departure Location: Upper West Side

Cross Country Ski & Snowshoe Trek

Saturday, February 14

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

Departure Location: Union Square

Mount Washington Winter Summit

Saturday, February 14

Put your fitness and skills to the test on this challenging, rewarding climb to of the highest peak in New Hampshire.

Pickup Location: Upper West Side

Snowshoe & Wine Tasting

Sunday, February 15

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

Winter Horseback Ride & Wine Tasting

Sunday, February 15

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

Departure Location: Upper West Side

Snowshoe & Hound

Saturday, February 21

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

Departure Locations: Union Square & Upper West Side

Snowshoe Hike & Whiskey Tasting

Saturday, February 21

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

Departure Location: Union Square

Cross Country Ski & Snowshoe Trek

Sunday, February 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, February 23

Experience Africa in a meaningful way

Wilderness First Responder Certification

Friday, February 27

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.

Cross Country Ski & Snowshoe Trek

Saturday, February 28

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

Departure Location: Union Square

Winter Horseback Ride & Wine Tasting

Saturday, February 28

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

Departure Location: Union Square

Snowshoe & Wine Tasting

Sunday, March 1

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

Ice Climbing

Sunday, March 1

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

Departure Location: Upper West Side

Wilderness First Responder Recertification

Thursday, March 5

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.

Ice Climbing

Saturday, March 7

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

Departure Location: Upper West Side

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

Cross Country Ski & Snowshoe Trek

Sunday, March 8

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 9

Experience Africa in a meaningful way

Catskills Hike: Indian Head Mountain

Saturday, March 14

Gorgeous trail and sweeping views!

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

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

Snowshoe & Brew

Sunday, March 22

Snowshoes and a pint

Departure Location: Union Square

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

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

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

Guides' Choice: Tammany Mountain

Saturday, April 4

Challenging hike to amazing views of the Delaware Water Gap

Departure Location: Union Square

Night Hike

Saturday, April 4

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

Departure Location: Penn Station Area

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

Fourteen Peaks Hike

Saturday, April 11

Fantastic twelve-mile challenging ascent of 14 peaks.

Departure Location: Upper West Side

Great preparation for Guide’s Choice hikes

Millbrook Mountain & Lake Minnewaska

Saturday, April 11

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

Departure Location: Upper West Side

Rock Climbing

Sunday, April 12

Rock Climb the legendary Shawangunk Ridge. No experience necessary.

Departure Location: Upper West Side

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.

Guides’ Choice Hike: Blauvelt Mountain

Saturday, April 18

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

Departure Location: Upper West Side

Clydesdale Horseback Ride & Brewery

Saturday, April 18

Ride majestic clydesdales through the countryside.

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

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

Surprise Lake Hike

Saturday, April 25

A stunning day hike.

Departure Location: Upper West Side

Hike & Whiskey Tasting

Saturday, April 25

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

Catskills Hike: Indian Head Mountain

Saturday, April 25

Gorgeous trail and sweeping views!

Departure Location: Upper West Side

Horseback Riding & Wine Tasting

Sunday, April 26

Ride through forest and fields. Sample wines and ciders

Departure Location: Upper West Side

Raccoon Brook Hike

Sunday, April 26

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

Departure Location: Upper West Side

Hike & Brewery Tour

Saturday, May 2

Hiking and a pint

Departure Location: Union Square

Awosting Falls

Saturday, May 2

Moderate nine-mile hike to idyllic waterfalls

Departure Location: Union Square

Schunemunk Mountain Hike

Sunday, May 3

Unique Rock Formations and Scenic Views

Departure Location: Upper West Side

Hike & Howl

Sunday, May 3

Hike on the Kittatinny Ridge then explore a wolf sanctuary

Departure Location: Union Square

Africa Volunteer Trip Aiding Elephants

Monday, May 4

Experience Africa in a meaningful way

Hike & Wine Tasting

Saturday, May 9

Stunning Views and New York Wine to Taste

Departure Location: Union Square

Night Hike

Saturday, May 9

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

Departure Location: Upper West Side

Storm King Mountain

Sunday, May 10

Sweeping views of the Hudson River and Valley

Departure Location: Union Square

Horseback Riding & Wine Tasting

Sunday, May 10

Ride through forest and fields. Sample wines and ciders

Departure Location: Upper West Side

Diamond Mountain Hike

Saturday, May 16

Gorgeous, moderate six-mile hike in Harriman State Park

Departure Location: Union Square

Guides’ Choice: The Great Escape

Saturday, May 16

A historical hike on the Appalachian Trail

Departure Location: Upper West Side

Hike & Brewery Tour

Saturday, May 16

Hiking and a pint

Departure Location: Union Square