Fall in the Hudson Valley may be a popular time to hike, but I’d argue that the region’s best leaf-peeping happens from the seat of a bike. We have trails that cross the Hudson River, trace the foot of the Catskills, flank reservoirs and wetlands, and take riders through tunnels of vibrant foliage. The views can be downright epic, and the crisp, cool weather makes you feel like you could pedal all day. Plus, cycling lets you relish the fall colors without sitting in traffic — or creating pollution.
Whether you’re an avid cyclist or feeling inspired to dust off the bike in your garage, this is the perfect season to explore the Hudson Valley on two wheels. Here is the lay of the land and some highlights you’ll find along each trail.
Dutchess Rail Trail
The Dutchess Rail Trail runs 13.4 paved miles from Hopewell Junction to Poughkeepsie, offering one of the smoothest and easiest rides in the region. Start at the Hopewell Depot Museum, where you can learn how this former rail line once took passengers and freight across the Hudson Valley. From there, the wide, mostly level path winds past wetlands, horse farms, and leafy green spaces — with plenty of benches and convenient stopping points along the way. You may even catch a whiff of freshly baked cookies from a nearby bakery or spot wildlife. I’ve seen turtles, deer, rabbits, herons, and the occasional cat here.
Save some energy for the end of the ride. Although the Dutchess Rail Trail officially ends in Poughkeepsie, the path continues directly onto the Walkway Over the Hudson. Pedaling across the world’s longest elevated pedestrian bridge feels like taking a victory lap, especially in fall, when both sides of the valley are ablaze with color. If you need to rehydrate, you can find bottle refill stations at either end of the walkway.
Harlem Valley Rail Trail
For a quieter, more pastoral ride, head to the Harlem Valley Rail Trail. The 26-mile paved route begins alongside the Metro-North Railroad tracks in Wassaic and ends on the outskirts of Hillsdale, with plans to eventually extend it to Chatham. One minute, you’re pedaling over boardwalks tucked into dense greenery. The next, the trail opens up to rolling farmland and mountain views. It also tends to be less crowded than the Dutchess Rail Trail, which makes it easier to spread out if you’re riding with someone else.
Millerton makes a natural turnaround point if you’re not up for riding the entire trail. Bike racks and public restrooms make it easy to stop there for lunch. Harney & Sons is a smart choice for iced tea and gourmet sandwiches right next to the trail. On Saturdays, you can also swing by the nearby farmers’ market for fresh fare. If you continue north, you can turn the ride into a full-day outdoor adventure at Taconic State Park and take a short hike to Bash Bish Falls.
Wallkill Valley Rail Trail
Few other rail trails capture that quintessential fall vibe quite like the Wallkill Valley Rail Trail. The 23-mile trail runs from Gardiner to the Kingston city line, taking riders through apple orchards, across the Wallkill River, and over the spectacular Rosendale Trestle. Standing 150 feet above Rondout Creek, it was the tallest span bridge in the country when it originally opened to rail traffic in 1872. Today, it offers some of the best views in the Hudson Valley, especially when the trees have turned red and gold.
New Paltz makes a fun stop along the way. With college back in full swing, the town buzzes with back-to-school energy and has plenty of places to grab lunch. Or keep riding to the Rail Trail Cafe, a seasonal outdoor spot tucked into the woods that feels like a secret hideaway. One thing to know before you go: This trail has a crushed-stone surface, so you’ll do better tackling it with a gravel or hybrid bike.
Ashokan Rail Trail
Some of Ulster County’s prettiest scenery can be found along the Ashokan Rail Trail, an 11.5-mile crushed-stone path between West Hurley and Boiceville. It offers panoramic views of the Catskills and the Ashokan Reservoir, which supplies approximately 40 percent of New York City’s drinking water. Keep an eye out for bald eagles soaring above the water.
While the reservoir is the star of the show, it’s not the only reason to ride here in fall. Parts of the trail take you into the forest, where changing leaves surround you in every direction. Interpretive panels along the way share fascinating tidbits about the reservoir and the communities that were displaced when it was constructed over 100 years ago, giving you plenty to ponder as you pedal.
Maybrook Trailway
Head southeast from the Hopewell Depot Museum and you’ll hit the Maybrook Trailway, an off-road route that runs for about 23 miles to Brewster. It feels more remote than many of the region’s rail trails, taking riders through long stretches of dense woods and past farms, ponds, and wetlands. You’ll even cross paths with the Appalachian Trail near Pawling (look out for the white trail marker). In the fall, the forested sections are especially stunning — and with relatively few crossroads, the ride takes on a meditative quality. You can just go and go as the colors surround you.
The most scenic part of the trail is the stretch along Whaley Lake, where the path follows the shoreline and continues on a causeway over the water. In fall, the colorful hills reflected in the lake make this part of the ride feel dreamy. You’ll also pass Ice Pond and Lake Tonetta as you get closer to Brewster. Just come prepared: Services are scarce between Hopewell Junction and Brewster, so bring plenty of water and snacks.
Heritage Trail
The Heritage Trail offers a little bit of everything across its 19.5 miles between Middletown and Harriman. Built along the former Erie Railroad, the mostly paved route shifts between shady woods, open meadows, streams, and towns. The trail also passes by the 6½ Station Sanctuary, a 62-acre marshland preserve where more than 200 species of birds have been spotted.
The trail makes it dangerously easy to turn your fall bike ride into a brewery outing. In Chester, hop off for a drink at Rushing Duck Brewing Company, a small, family-run brewery near the trail that frequently hosts live music. Check the calendar before your ride to see what’s happening.
Albany County Helderberg-Hudson Rail Trail
Worth a trip north, this lovely nearly 10-mile paved trail follows the old D&H Railroad Line, connecting the communities of Voorheesville, New Scotland, Bethlehem, and Albany. While previously it was often used as an out-and-back option, a newer link between the previous trail end on South Pearl Street on Albany’s south end and the Corning Preserve along Albany’s stretch of the Hudson now connects the trail to the Mohawk Hudson Bikeway on the Empire State Trail.