Harlem Valley Rail Trail

Take a pedal-powered trek through forest and field, and get some shopping in, too.

Photo by Mike Todd, Hike the Hudson Valley

Wassaic Station to orphan farm meadow

Wassaic Station/Harlem Line to Amenia to Millerton (Dutchess),10.7 miles; paved
Under Mountain Road to Taconic State Park & Orphan Farm Meadow (Columbia), 4.9 miles; paved

It’s a trail of two counties, totaling 15 paved miles in Dutchess and Columbia. Once the tracks of the old New York and Harlem Railroad, this rural route is a great all-day ride — or one you can do on two consecutive half-days. Savvy cyclists park a second car at the Millerton end so that they can hop behind the wheel and drive north to pick up the trail in Columbia County at Under Mountain Road, just off Route 22. Alternatively, it would take about an hour by bike, and involves riding on Route 22.

9 a.m.

Begin at the Wassaic Station in the Metro-North parking lot. After 2.5 miles (15 minutes or so), take a detour to Mechanic Street in Amenia. You can’t miss the bright blue-painted Blueberry Hill Galleries, an estate sale service with a Tag Sale Shop for browsing. Turn the corner to the main drag (aka Route 343), where you can eat in or grab a to-go sandwich or panini at Back in the Kitchen.

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10:30 a.m.

Return to the trail and enjoy the scenic, almost 4-mile stretch from Coleman Station north to Millerton, with the Webutuck River and Ten Mile Creek running alongside. The raised, “pyramided” rail bed gives you nice farmland views as well.


11 a.m.

At the Millerton terminus, check out a rescued circa-1858 Irondale Schoolhouse repurposed as a seasonal information center. Take a seat at the trailside picnic tables of the community center to enjoy your lunch or just take a breather. No picnic? Try the retro-styled Oakhurst Diner or Harney & Sons tea tasting room for world-class blends — hot or iced — along with sandwiches and soups.


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If it’s a Saturday, enjoy the Millerton Farmer’s Market, a short walk up Main Street to Dutchess Avenue. Stop at Oblong Books and Music and The Millerton Antiques Center, with more than 30 dealer stalls. Remember to save some energy for the hour-long, almost 11-mile bike ride back, if you didn’t park that second car here.

Oblong BooksPhoto by Parks & Trails New York

2:30 p.m.

Rested and raring to go — assuming you’re doing this all in one day and are buzzing around between trailheads by car — head to Under Mountain Road in Copake: Traveling along Route 22, it’s a distance of 8.6 miles (less than 15 minutes) from Millerton, if you parked a car there. Alternatively, it’s 20 miles (half hour) from the Wassaic Station, if you head back there to pick up your vehicle. Heed the signs for timber rattlesnake habitat and red foxes on this pretty path, and bear in mind that there will be a blip of dirt road for less than half a mile. Along the way, you’ll cross two streams and enjoy Catskills views.


Harlem valley rail trail

3:15 p.m.

Arrive at Taconic State Park at Copake Falls. (Plan B could be to camp in the park and rent a bike here at Bash Bish Bicycle.) If you’re famished again, visit Depot Deli right across the street. This former train hub serves cinnamon buns, sandwiches, and salads to go. Check out the working model Lionel railroad. Bash Bish Falls is only 1 mile by foot, just over the Massachusetts border, a nice side trip.

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4:30 p.m.

Follow signs within the park to Copake Iron Works Historic District, which operated from 1845 to 1903 and has its own museum. If time allows, take a dip at Ore Pit Pond (Memorial to Labor Day) followed by a beachside lunch.


5:30 p.m.

It’s a short ride (1.2 miles) to Orphan Farm Meadow, which features a nice parking area with benches and an original rail marker to signal the completed trail’s end. Afterward, hightail it or meander back (30 to 60 minutes to Under Mountain Road). Collapse into the car, then treat yourself to a steak dinner at The Pond Restaurant in Ancramdale, or drive 15 minutes north up Route 22 for traditional Wienerschnitzel on the patio at Swiss Hutte Inn and Restaurant near the Catamount Ski Area/Adventure Park in Hillsdale.

Trail Info: http://hvrt.org

Go the Extra Miles

This spring, Dutchess County announced that it received a $3.5 million grant from the Federal Highway Administration to extend the Harlem Valley Rail Trail almost nine miles north from Millerton to Under Mountain Road. That means we should soon be able to ride the trail for 23 gorgeous, uninterrupted miles. Woohoo!

harlem valley rail trailPhoto by Parks & Trails New York

Pit Stops

Blueberry Hill Galleries
35 Mechanic St, Amenia
845.240.4795; www.blueberryhillgalleries.com

Back in the Kitchen 
3312 NY-343, Amenia
845.789.1444; Find them on Facebook

The Irondale Schoolhouse
16 Main St, Millerton
518.789.4619; www.irondaleschoolshouse.org

Oakhurst Diner
19 Main St, Millerton
518.592.1313; www.oakhurstdinerny.com

Harney & Sons 
13 Main St, Millerton
518.789.2121; Find them on Facebook

Millerton Farmer’s Market
Main St and Dutchess Ave

Oblong Books and Music
26 Main St, Millerton
518.789.3797; www.oblongbooks.com


Millerton Antiques Center
25 Main St, Millerton
518.789.6004; www.millertonantiquescenter.com

Taconic State Park Copake Falls
253 Rt 344, Copake Falls
518.329.3993; www.parks.ny.gov/parks/83/details.aspx

Bash Bish Bicycle 
247 Rt 344, Copake Falls
518.329.4962; Find them on Facebook

Depot Deli
64 Miles Rd, Copake Falls
518.329.4770; Find them on Facebook

Bash Bish Falls
413.528.0330; www.mass.gov

Copake Iron Works Historic District

The Pond Restaurant
711 County Rt 3, Ancramdale

Swiss Hutte Inn and Restaurant 
3290 MA-23, Hillsdale
413.528.6200; www.swisshutte.com


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