Cidiot’s Favorite Dog Walks in the Hudson Valley

Easier access to the outdoors and stunning walks is a feature of moving from the city to the country. You don’t need to have a lot of property to really get outside. Now, cidiots need to learn the difference between a “hike” and a “walk.” As you hopefully heard in Episode 55 Take Your Own Hike, from our expert guest, a hike requires elevation—and sometimes a touch of danger!.

For my walks with Nora, they are definitely walks, I’ve been building a circuit mixed with routine (she likes) with variety (for me), and for the weather (critical in upstate New York).

I’ll list my favorite discovered walks so far from both places we have lived, with contributions from listeners as well. I’m starting with the east side of the Hudson in Northern Dutchess and Columbia County, so please help me with your favorites for the wider map.

Bring with you: Sunscreen, hat, water, plus keep a travel water bowl in your trunk for afterwards for the dog.

COLUMBIA COUNTY

These first ones in Columbia County are all amazing river views:

Columbia Land Conservancy - Greenport: Walk to the River
319 Joslen Blvd, Hudson, NY 12534 | Use the CLC hike locator 

Six miles of trails here, although Nora and I usually just take the nearly-straight shot from the small parking lot off Joslen Blvd to the Hudson River. Along the one-mile walk, we passed through a bird sanctuary, fields, and got stunning Catskill Mountain views. A few choices along the way of paths, but bear left at the giant squirrel sign, and you should find a pagoda right along the river where you can stop. If you and the pup still have energy, keep going along the other paths north to find more stops. 85% of the walk is exposed, so bring a hat and wear sunscreen.  See the picture above.

Harrier Hill Park: A View High Above the River
6729 Rod and Gun Rd, Hudson, NY 12534 | Site 

On days the weather is sketchy or bad, and I just want a very short walk and a view, I take Nora to Harrier Hill Park. Managed by Scenic Hudson and just north of Walmart on Fairview Avenue, make a sharp left at the Atlantic Avenue light and head to the very end of Rod and Gun Road. There’s a lot for the park and a super-short walk up to a terrific Hudson View and tons of places to sit. There’s a covered space as well which is probably used for weddings and events. This would probably also be good for older dogs.

Olana Historic Site: Frederic Church’s Home
5720 State Route 9G, Hudson, NY 12534 | Site

Step into a painting! Get to know this amazing space through Episode 132: Walking Olana. Several miles of walking trails run along the property and up and down the hill from the iconic house and home of the Hudson River School of painting. Popular among dog owners and walkers, there’s an Instagram feed #dogsofolana.

Clermont Historic Site: Mansion Above the River
1 Clermont Avenue, Germantown, NY 12526 | https://www.friendsofclermont.org/ | Trail Map 

Nora was a weekly visitor here, especially when we lived near Tivoli. Clermont, home of the Livingstons (featured in Episode 21 https://www.cidiot.com/21-freedom-begins-between-the-ears/), offers a few different walks. The one we take the most is parking in the big guest lot, we walk along the Hudson River (up above the Amtrak line), up and down the slopes with picnic tables, stop at the signs that tell the history (e.g., “A River Highway”) around the grounds of the mansion, through the garden and back to the lot. The other walk is more nature-filled, parking in the lot, but heading south along the river is a wonderful path that will loop around and bring you back through more of the open grounds of Clermont. 

Here are two few walks I’ve discovered further inland in Columbia County

Won Dharma Center: Views from the Nirvana Trail
361 Route 23 Claverack, NY 12513 | Site

Nora is also a regular here as well. As you drive in you’ll see there’s a parking lot before you get to the house that’s open to the public. Parking in this first lot on the right, you can choose among the flatter walks to the west that go into the woods by the water, or go up the hill as we usually do, for a choice of a 1-mile or 2-mile-plus hike. We usually walk up to the right on the Nirvana Trail, which has a modest incline through the woods before hitting the open space with a view first west, then south along Route 23, then east to the Berkshires. The path brings you back into the woods, where you can continue on another mile or two in the loop or go left (Nora is usually wiped) and head downhill back to the parking lot. There are little maps you can peek at to plan your wandering.

Roeliff Jansen Park
116 Old Rte 22, Hillsdale, NY 12529 or just off Route 22, half a mile south of Hillsdale hamlet, Hillsdale, NY | Site

This is a Saturday favorite: walking Nora up the one- or two-mile loop, then ending at the Copake-Hillsdale Farmers' Market in the parking lot. Great views of the Berkshires to the east and the Catskills to the west. There's a small dog run, too.

DUTCHESS COUNTY

Greig Farm
227 Pitcher Lane, Red Hook, NY 12571 | Site 

Nora was a weekly regular here when we lived nearby. It's also mentioned on many Cidiot episodes. Walk the farm trails through the orchard and then stop into the daily market store. This is great if you want a simple flat walk through beautiful property, with the option for shorter loops (and older dogs). 

Poet’s Walk Park
776 River Rd, Red Hook, NY 12571 | Site 

According to Scenic Hudson, who manages the property, it was “created for the owners of two neighboring estates around 1850. It got its name because writers like Washington Irving loved rambling here; legend has it he came up with the idea for “Rip Van Winkle” while gazing toward the Catskill Mountains, site of his protagonist’s long sleep.”  Starting at the parking lot, there’s a nice loop up to the “Overlook Pavillion” with a great view, out to the water for more, then back down through the woods. Or go reverse. 

Burger Hill at Drayton Park

3158 NY-9G, Rhinebeck, NY 12572 | Site

Wonderful place for a short hike with the dog with slight elevation. Just outside Rhinebeck, managed by Winakee Land Trust, you’ll pull into a small lot for the park and can hike the hill from one of two directions. I usually do the one on the left side which is a gradual way up under some trees, then be surprised by the stunning view of the Catskill Mountains. Up top you’ll see some rocks with carvings to tell you which mountain you’re looking at. Then you can go back down the other side of the slope. 

Staatsburgh Historic Site in Ogden Mills and Ruth Livingston Mills State Park
75 Mills Mansion Drive 1 Road, Staatsburg, NY 12580

On the grounds of this Beaux-Arts mansion (think Downton Abbey), south of Rhinebeck, north of Hyde Park, you can walk around and get right to the river. It’s rare to get to the water since the Amtrak line prevents most homes from having direct access. These folks were so wealthy that they had the train line go behind the house. You can hike through the woods as well. 

Stissing Mountain Fire Tower
499 Lake Rd, Pine Plains, NY 12567 | Site

This spot was recommended by a user on Reddit. “The Stissing Mountain Fire Tower is my go to with dogs. Weekdays it’s pretty empty and that’s good for me because my dogs can get testy with other ones. It’s quick, but fairly steep”

PUTNAM COUNTY

Fahnestock Memorial State Park - The Charcoal Burners Trail
1498 NY-301, Carmel Hamlet, NY 10512 | Site

Another recommendation in the Reddit Hudson Valley group. The Charcoal Burners Trail in Clarence Fahnestock Memorial State Park (Putnam Valley, NY) is a scenic, moderately challenging 6.2-mile loop. It features dense woodlands, quiet streams, and Beaver Pond. “Charcoal Burner's Trail (Fahnestock) is a goody! Varied terrain, including field and forest, passing by several bodies of water in case doggo needs a dip. Beaver Pond is about a mile north of the trailhead, and can be great for a dip.”

ULSTER COUNTY

Ashokan River Promenade

Olivebridge | Site

Paved and flat, this is a 2.8-mile walk with your dog (or bike) along a stunning piece of water, the shore of the reservoir.

Minnewaska State Park Preserve
5281 Route 44-55, Kerhonkson, NY 12446 | Site

Also recommended by Hudson Valley Reddit users. The Minnewaska State Park Preserve is a 23,974-acre preserve located on the Shawangunk Ridge in Ulster County, New York on US 44/NY 55, five miles west of New York State Route 299. Many trails to choose among, some might be better with dogs than others. 

Frequently Asked Questions: Dog Walking in the Hudson Valley

Q: Are dogs allowed off-leash at major historic sites like Olana or Clermont?

A: Generally, no. Most state historic sites, parks, and preserves in the Hudson Valley strictly require dogs to be on a standard leash (usually 6 feet or less). This keeps local wildlife safe, protects historic grounds, and ensures a good experience for everyone. If your dog needs to burn off steam entirely off-leash, you’re better off checking out dedicated community spaces like the Rhinebeck Dog Park, Hudson Dog Park, Germantown Dog Park, or the Gardiner Dog Park.

Q: What’s the deal with ticks Upstate, and how do I protect my dog on walks?

A: Ticks are a year-round reality in the Hudson Valley, even on wide gravel paths or lawns near the river. Stick to the center of the trails, avoid high brush, and always do a thorough belly-and-paw check before letting your pup back into the car. Keeping your dog up to date on veterinarian-recommended preventative treatments is essential out here.

Q: Do I need to bring my own poop bags, or are there stations at these sites?

A: A golden rule of country life: Leave No Trace (and pack it out). While popular spots like Olana and Clermont often have waste stations near the main parking lots, you can’t always count on finding them mid-trail. Always carry your own bags, and prepare to take them with you if a trash receptacle isn’t nearby.

Q: Where can we grab a coffee or a bite with the dog after a walk?

A: The Hudson Valley is incredibly dog-friendly, and many local spots love welcoming four-legged hikers. If you're near Hudson, you can swing by specialty coffee shops on Warren Street or visit pet-focused local business owners like Patrick at Lily’s Natural Pet Store to stock up on treats. If you’re further south near Rhinebeck, stop by Pause Dog Boutique to grab some special snacks for a post-walk reward. Say hi.

Q: Are there any seasonal closures or parking fees I should watch out for?

A: While trail access is often open year-round, parking fees can vary. State parks and historic sites sometimes charge a vehicle use fee during peak weekends, spring through autumn, though walking the grounds out-of-season is frequently free. Always check the official site maps (like the Clermont Trail Map) before you head out to verify seasonal hours or specific parking lot directions.