The 8 Best-Reviewed and Most-Instagrammed Hikes Near Rhinebeck, NY

One of the most time-honored activities of the Hudson Valley is hiking. From the Native American tribes, to the Thomas Cole era of Hudson River School landscape painting, to the era of Gilded Age mansions with public grounds, and publicly-owned parks and nature preserves, there’s been a shared lineage of appreciating nature, having deep thoughts and spending quality time with loved ones while getting some exercise.

If you’re staying in Rhinebeck, NY and you want to check out some local trails and hikes, here’s what local hikers are recommending the most:

1. Poet’s Walk Park

562 Reviews
4.8 Average Stars
11,600 Instagram Posts
Distance from Whistlewood: 5.7 Mile Drive

Poet’s Walk was created around 1850, with a deliberate landscape design for two neighboring estate-holders. However, what put it on the map was its notoriety for Hudson Valley writers like Washington Irving, of Rip Van Winkle fame, walking around and drawing inspiration from its unobstructed views of the Catskills mountains. It’s considered an easy to moderate hike, and there’s also an iconic gazebo known as the Summer House.

2. Ferncliff Forest

418 Reviews
4.8 Average Stars
8,598 Instagram Posts
Distance from Whistlewood: 5.4 Mile Drive

Ferncliff Forest started out as a small part of John Jacob Astor’s estate, when he was the richest man in the United States by the time of his death in 1848. It was donated to the Rhinebeck Rotary Club in 1964 with the stipulation that it would remain “forever wild.” There are about 12 miles of trails, varying if difficulty, with the highlight being the 80-foot fire tower that was constructed in 2007. It provides views of the Hudson River, the Catskill Mountains, and the nearby Kingston-Rhinecliff bridge.

3. Black Creek Preserve

342 Reviews
4.7 Average Stars
5,476 Instagram Posts
Distance from Whistlewood: 19.2 Mile Drive

Across the Hudson River, Black Creek Preserve is a 130-acre natural area that has a network of trails that feature a dramatic suspension bridge, seasonal vernal pools, scenic views of the Hudson River, and some challenging steep sections that help you earn your dinner afterward.

4. Esopus Meadows Preserve

225 Reviews
4.7 Average Stars
2,503 Instagram Posts
Distance from Whistlewood: 16 Mile Drive

Esopus Meadows Preserve is a 96-acre park in Ulster Park, also located on Route 9W near Black Creek Preserve. This one has a quicker, easier hike than Black Creek Preserve, with views of the Hudson River, the historic Esopus Meadows Lighthouse, and birdwatching opportunities.

5. Drayton Grant Park at Burger Hill

173 Reviews
4.8 Average Stars
4,152 Instagram Posts
Distance from Whistlewood: 2.6 Mile Drive

This one is pretty simple. It’s a giant 550 foot hill, with under a mile of hiking available, but at the top you get panoramic views of the Hudson Valley, including the Catskill Mountains and Berkshire Mountains. In the winter, it’s a great place to go sledding.

6. Thompson-Mazzarella Park

98 Reviews
4.5 Average Stars
50 Instagram Posts
Distance from Whistlewood: 3.6 Mile Drive

Managed by the Winnakee Land Trust, this park has a little over two miles of loop trails that go through agricultural fields and forests. There are soccer fields and a playground for children.

7. Kingston Point Rail Trail

88 Reviews
4.6 Average Stars
304 Instagram Posts
Distance from Whistlewood: 12.8 Mile Drive

There is a 2 mile trail along the water in Kingston, right across the Kingston-Rhinecliff Bridge. It also connects to Kingston’s network of trails, like the recently opened Hudson River Brickyard trail. On the weekend, you can also take a historic ride into Downtown Kingston using the Kingston Trolley, which preserves working trolley trains from over 100 years ago.

8. Hopeland Trail

42 Reviews
4.7 Average Stars
29 Instagram Posts
7.5 Mile Drive

This trail has a quick, 1.5 mile round trip, and can take about 30-40 minutes to complete. There’s a tranquil pond and benches for rest and contemplation. It’s within Mills-Norrie State Park, which has several more trails, a golf course, and the Staatsburgh State Historic Site that features a Beaux-Arts mansion from the Gilded Age.