Things to Do Outdoors in Upstate New York

Updated: March 2022. Now that the days are getting longer and filled with more sunshine, it’s time to think about things to do outdoors in upstate NY. Here are some great choices for you, no matter your level of fitness. We include some hiking, horseback riding, and kayaking–all with some great views and interesting sites added in.

Don’t forget to plan this adventure with a place to rest your head in the evening. Caldwell House will pamper you with super comfortable bedding and start your day with an amazing breakfast to prepare you for another day of exciting outdoor adventures.

Hiking Adventures

One of the best things to do outdoors is simply taking to trails. It’s an amazing way to get out in nature with the rebirth of springtime blooms and a great form of exercise. Please make sure to connect with us if you can’t decide which of the many trails is the best fit for you! Each of these trails is a 30-minute drive or less from Caldwell House.

Hudson Valley Rail Trail

This 7.1-mile trail (4 miles of which is paved) takes you through hardwood forests, under two spectacular stone-arched bridges with some great spots for spring-blooming wildflowers. The east end of the trail meets the Walkway over the Hudson which gives you amazing views of the Hudson from a vantage point of 200 feet above the water.

Anthony’s Nose

For a moderately challenging hike, this1.9 mile out and back piece of the Appalachian Trail is a stone staircase that will reward your efforts with a gorgeous view of the Hudson. Bring a picnic lunch to enjoy on the flat rocks at the top of the trail.

Carnwath Farms Historic Site and Park

One of the unique things to do outdoors in upstate NY is a hike at the Carnwath Farms historic site and park. The manor and carriage house were both built in the late 1800s and are beautiful examples of Italianate and French-style architecture. The park spreads over almost 100 acres and includes a number of interesting places to see and a network of trails that offer a spectacular view of the spacious NY countryside.

Shunnemunck State Park

If you can get over trying to say Shunnemunck State Park, you will enjoy the 3,300 acres of parkland! There are 8 marked trails totaling over 20 miles, some with elevations of over 1600 feet.

Kayaking Adventures

 If you bring your own kayak, there are some launching sites in Patterson and Putnam County, some with a bit of a hike before you can set down. For those seeking an easier route, you can try the lower Esopus or Tivoli Bays.

For a bit of adventure, kayak to Bannerman Castle and take a tour of the ruins and gardens. If you plan it right, you could be there for a concert!

If you don’t have your own equipment, no worries! Storm King Adventures has more than a dozen guided tours (including to Bannerman Castle, if that intrigues you). There are tours with lookouts for bald eagles, full moon, and sunsets — lots to choose from!

Riding Adventures

Whether you’re seeking some solitude or a fun “family bonding” time, a trail ride is a perfect way to spend the day during a stay at the Caldwell House Bed and Breakfast. We’ve got some fantastic options for horse lovers that are close to our inn. Lessons, rides, and more are available for all ages and skill levels.

Ivy Rock Farms
New Windsor, NY
6 minutes from our B&B

Owner Shelley Gray, started Ivy Rock Farms 30 years ago with the goal to provide a facility that allows children and adults from all walks of life, to enjoy horses safely, affordably, and with excellent instruction. Take a 60-minute private lesson or one of their “learn to ride” packages. They also offer 90-minute or two-hour trail and gaming lessons. 

Twin View Stables
Campbell Hall, NY
15 minutes from our B&B

Twin View Stables is a family-run business welcoming all ages and skill levels. Their gorgeous property is located on 60-acres of land on top of a hill that offers riders panoramic views and beautiful trails throughout the woods. Choose from a wide range of services including riding lessons, training and trail rides, and seasonal events throughout the year.

Juckas Stables
Pine Bush, NY
30 minutes from our B&B

For a fantastic trail ride, Juckas Stables offers rides that show off the scenic Hudson Valley. Take advantage of their very popular 45-minute trail ride with an experienced guide who will take you around 117 acres of rich farmland and trails. The trail rides limit the horses to either walk or occasionally trot. Their staff will also help you take photos along the way! Check out their Date Night Ride!

Westchester Trail Rides
Croton-On-Hudson, NY
40 minutes from our B&B

With acres of beautiful untouched land, you will have a memorable experience with the folks at Westchester Trail Ride. Ethan Capshaw, known as “The Trailmaster,” knows every inch of the property and also speaks four languages which helps with visitors from foreign lands! Contact them for more information on trail ride rates and anything else you need to know for a comfortable day on the trails.

With so many things to do outdoors in upstate NY, you are going to want to plan several days for your stay! So don’t wait, and book now. If you have any questions at all, we are happy to help you plan your fun itinerary.


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