Day Trips
Halloween Horseback Riding & Wine Tasting

Costumes optional! Ride Through Forest and Fields; Sample Wines and Ciders with Live Acoustic Music

Get your costume ready! We’re going to have fun this Hallowe’en, atop horses. Join Outdoor Bound for a day of riding and wine tasting. Start with a lovely drive upstate to the stables, which sit on hundreds of wooded acres and boast some of the best riding trails in the Northeast.

Headless Horseman is the obvious costume choice…what else can you come up with?

After a short safety briefing, get acquainted with your horse. The lively but well-mannered horses have names like Uno, Dos and Tres; there is even an all-white pony called Gringo.

We will saddle up, then ride for two hours through fields and woods with an experienced wrangler. All skill levels are welcome and trotting is allowed. The land is a wonderful mix of rocky terrain, hills and some narrow paths as well as wide-open fields.

Next, we will drive to a beautiful vineyard in the Hudson Valley for a wine tasting. Enjoy a sample of reds and whites along with some of the best hard ciders in America. Listen to the winery’s live acoustic music while you eat and afterwards stroll around the vineyard grounds or enjoy a bottle of wine.

Costumes optional; but the best costume wins a bottle of wine!

Event Details

Depart 9:00 AM at the corner of 73rd Street and Broadway. Arrive at 8:45 AM for check-in!
Return Approximately 5:30 PM, same location
Wear Pants or jeans for riding; jacket or coat, comfortable shoes or boots; hat and gloves in spring or variable weather.
Bring Snacks and water. You may bring your lunch or purchase lunch from the CIA-trained bakery.
Please note: all participants must weigh less than 250 lbs.

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Experienced, Fun & Qualified Guides

From cycling across the United States to leading horse treks through New Zealand to scaling Nepalese peaks, Outdoor Bound guides have real-world outdoor experience. Collectively, they have hiked, biked, climbed and kayaked tens of thousands of miles around the globe.

Whether their professional backgrounds are as teachers, personal trainers, artists, environmentalists or business leaders, they all have an extensive knowledge of the natural world and local history. Each guide has also passed a rigorous guide certification program and is trained in wilderness first aid or as a Wilderness First Responder.

Diverse & Interesting Groups

There is no typical Outdoor Bound participant. While ages typically range from 20 to 50, those who come to experience outdoor adventure range from singles to couples, from lawyers to waiters. They are a mix of women and men. While the group is always diverse, you will certainly feel welcome. Our guides go the extra mile to make the atmosphere of each trip social and fun. Many people in the Outdoor Bound community have forged lasting friendships as a result of our trips.

New Experiences

Skydiving, ice-climbing, hot-air ballooning, skiing and hiking every weekend are just a few of Outdoor Bound’s year-round adventures. These trips are accessible to everyone, including the novice, who might feel a little uneasy, the young urban professional trying to get away and even the adrenaline junkie looking for a new rush.

Environmental Awareness

“Leave nothing but footprints, take nothing but pictures,” is the Leave No Trace motto embraced by Outdoor Bound. From purchasing bamboo T-shirts to printing with soy-based inks on recycled paper, Outdoor Bound strives to create the least environmental impact possible while on trips and in the office.

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Bringing a Friend or Two?

Please be sure to enter the total number of people in the Qty box. In addition, be sure to include your friends’ names and cell-phone numbers on the final Checkout page. The final discount price is the price per person, multiplied by the Qty you enter.

Reminder about Trip Conditions

We closely monitor snow, ice and related weather conditions before each trip. Lack of snow or similar, unsatisfactory weather/trail/river conditions may lead to changes to the trip or rescheduling or cancellation.

Please consult the individual trip description or Event Calendar for notice of any such changes. Refer to our full Policies page for more information about reservations and cancellations.

Event Categories

Day Trips
Halloween Horseback Riding & Wine Tasting