by Jen Kiaba

As the summer fades away and the leaves start to change in the Hudson Valley, autumn ushers in a perfect time to lace up our hiking boots and hit the trails. The areas boasts an abundance of trails for hikers of every skill level and age, each with something unique to offer. Here are some of our favorites:

For those who are just getting started hiking, or who need easier trails, there are several rail trails that boast beautiful scenery while being easy on the joints. In southern Dutchess County hikers can enjoy the Dutchess Rail Trail, which is a 13 mile stretch that connects the former Hopewell Junction train depot with the Poughkeepsie entrance to the Walkway Over the Hudson. The paved trail runs through the towns of Poughkeepsie, LaGrange, Wappinger and East Fishkill.

From there, hikers can continue on across the Walkway Over the Hudson. The elevated bridge, which was converted from a formerly abandoned railroad bridge, gives hikers views of the valley from 212 feet above the river and spans 1.28 miles across the Hudson. The park has entrances in Poughkeepsie and Highland, with restrooms and picnic facilities on either side.

Another great hike with easy trails in Dutchess County is Poet’s Walk in Red Hook. Nearly two miles of trails wind around bucolic meadows and through woods that border the river. The first half mile to the Overlook Pavilion is an easy trail , which is great for kids. The rustic cedar pavilion sits on top of the highest hill in the park, rewarding hikers with a breathtaking view of the river valley. Throughout the trails there are also scenic footbridges, and benches to allow hikers to stop and take in the views.

To the north of Poet’s Walk is the Montgomery Place Estate in Annandale-on-Hudson, which offers woodland trails and garden paths along a 380-acre property for the enthusiast looking for an easy stroll. Further south in Hyde Park, hikers can find a 10-mile system of trails that links several National Historic Sites, such as the Home of Franklin D. Roosevelt, Vanderbilt Mansion and Val-Kill, as well as several town parks.

For a slightly more intense stroll, with a great reward at the top, Rhinebeck has Burger Hill. This short but steep climb ascends 200 feet in a little under a mile. The view, especially at sunset, is quite rewarding. And once the weather brings a layer of snow, this spot is especially popular for sledding.

Another popular hike boasting great views is Overlook Mountain in the Catskills. This five-mile roundtrip hike in Ulster County is considered moderately difficult and lasts around three hours. The rewards along the way are views of the Hudson Valley and the Ashokan reservoir, as well as the ruins of the old Overlook mountain hotel about two miles in.

Ulster County also boasts several hikes with unusual terrain. Nestled among the 85 miles of trails surrounding the Mohonk Mountain House is the Lemon Squeeze. For a fee, day hikers can traverse over five miles of trail that leads through a steep rock scramble and up to the Sky Top Tower. From there prepare to take in panoramic views of the Mohonk Preserve and Shawangunk Ridge. This hike is rated as difficult, and has some tight spaces so be prepared!

For those who don’t feel quite spry enough to squeeze their way to the top of of a trail, but want to enjoy breathtaking scenery, the Undercliff/Overcliff hike is a great alternative. Also part of the Mohonk Mountain House Preserve, there is a fee to hike this five mile loop. However the views of the Catskills and smaller ridges within the preserve make it a worthwhile outing. This former carriage road, as the name implies, brings hikers both over and under cliffs that are hotspots for local climbers.

And for those that want to take in a longer hike while enjoying a day at Mohonk, there is a junction in Overcliff Road that leads up to the mountain house. This makes for about a nine mile hike from the carriageway to the summit of the Sky Top Tower, so make sure to plan an entire day for this excursion!

Awosting Falls at Minnewaska State Park Preserve photo by Jim Gibbons

Awosting Falls at Minnewaska State Park Preserve photo by Jim Gibbons

While over in Ulster County, be sure to check out Minnewaska State Park Preserve. There are 35 miles of carriageways and 25 miles of footpaths, allowing for hikes at all levels. A great attraction in the preserve is Awosting Falls, which is a 60 foot waterfall in the Peters Kill Creek just inside the park. For those who want to take in several waterfall views within the preserve, the trails wind a little over eight miles past Awosting Falls, Castle Point, & Rainbow Falls. Though long, this is a moderate hike with a few small rock scrambles that would be suitable for young children up for a long walk.

For more breathtaking waterfalls, head into Greene County and check out Kaaterskill Falls between the hamlets of Haines Falls and Palenville. This two-drop waterfall is one of the more popular hikes in the Catskills, so be prepared for crowds during nice weather. The trail is accessed by two parking lots along 23A, both of which require a walk of about a quarter mile along to reach the trail head. So be aware of traffic as the shoulder is very narrow.

This is a moderately difficult but short hike, measuring two miles up and back. The Yellow Trail leads to the bottom of the falls, and signs warn of the perils of climbing further up. There is a trail to the right that led up to the top of the falls, but this has since been closed because of the dangers of falling off of the trail. It is highly recommended to end the hike at the end of the Yellow Trail, and enjoy the view of the

Kaaterskill Falls photo by Jim Gibbons

Kaaterskill Falls photo by Jim Gibbons

falls from there. An alternative is to drive to the top of the falls via Laurel House Road, which is off of the North Lake Road in Haines Falls, and access the view safely from there. Be advised, there is no safe or easy access to the bottom of the falls from the top and vice versa.

Another popular hike boasting a waterfall is Bash Bish Falls in Massachusetts. The hike has two parking lots, one in New York and one in Massachusetts, about a mile apart. The walk from the New York parking lot is about 1.5 miles and a flat, easy stroll. The hike from the Massachusetts parking lot is slightly steeper but about half a mile shorter. Either way the hike is about an hour, roundtrip, and the reward is a 60 foot waterfall, the highest in Massachusetts.

For more hikes in the area, or in-depth trail information on the hikes mentioned, is a great resource. The site offers step-by-step guides to nearly 60 recommended trails in the region, with Google Maps of all trail heads and photos of each hike documented. There are also two great search functions on the webpage: one to search the site, and another to search other webpages detailing great regional hikes such as,,,,,,,, and

Jen Kiaba is a photographer and writer based in Rhinebeck, NY. Her photography has been published internationally in magazines and on book covers. To see more of her work, visit

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