Orange Heritage Trail

On this half-day trek, you’ll cross paths with history, birds, good food, and a brewery while traveling through three charming communities.

Goshen to Monroe 

10 miles; paved

Bookended by country towns, this super-smooth pathway follows the rural route of the old New York & Erie Railroad, which boosted the region’s dairy industry and brought fresh milk to the masses in NYC in early 1840’s.

12 p.m.

Don’t believe any map that says the trail starts by Mary Harriman Park in Harriman. Not only is it not paved here, but there’s also a decrepit and dangerous bridge crossing nearby, so your real point of beginning is directly in the center of Monroe on Maple Avenue.  Why not eat first, cycle later? Festive La Rancherita will do nicely: a Mexican treasure serving shrimp burritos and torta sandwiches loaded with spicy pork and jalapenos. Or join the game-watching, pizza-eating, wing-munching crowd at nearby Gino’s. As you’re cruising out of town, we challenge you to resist Wally’s Ice Cream Parlor, a cute retro ice creamery known for its soft serve.

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1:30 p.m.

Minutes later, you’ll pass a park-and-ride facility where you can lock up your bike so you can poke around Museum Village, an open-air historical museum featuring vignettes of 19th-century life and hands-on activities like candle- and broom-making. Live chickens, too! (April-November)


3 p.m. 

About three miles onward is the 187-acre Jack and Louise Birnberg Preserve, an oasis for bird and amphibian watching. Next up, you’ll enter Black Dirt country, with its cornfields and tranquil scenery. Two miles from there you’ll arrive in the historic town of Chester and pull up alongside the Depot Museum, a restored stone 1915 building. Cool your wheels and explore local businesses like Outdoors, offering rugged footwear and trail-friendly clothing. Turn the corner and stumble upon Rushing Duck Brewing Co., a speakeasy-style hideaway where dogs, children, and outside food are all allowed.

Temptation strikes twice in the form of American House Ice Cream, renowned for milkshakes and root beer floats. Head up the block to Rustic Wheelhouse for grandma-style Italian and Clayton Delaneys Dining Saloon for classics like chicken cordon bleu and prime rib.


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Photo by Ken Gabrielsen

4:30 p.m.

Lush farm country unfolds as you parallel 17M for a spell (about four miles). Picturesque Goshen rewards you at the end of the line. Trailside Treats Creamery, a seasonal stand serving seriously good homemade ice cream, is outfitted with sun-shielding umbrellas and adorable child-size bistro tables, and is conveniently located along the path. Just give in already! It’s the perfect fuel to get you back to your car. If you’re in the mood for an early dinner instead, there are several good options on Main Street including Howells & Sunflower Café, which specializes in soups, smoothies, gluten-free wraps, and salads, and Craft 47, serving small-plate American tapas and Sunday brunch. Take note that Joe Fix Its Bicycle Repairs is also on Main Street if you need a part.


6 p.m.

Start your ride back. If you didn’t eat that early dinner, you could dine along the way, but you’ll probably want to head straight home to brag about your awesome day on Facebook.

Trail info:

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Pit Stops 

La Rancherita
101 Carpenter Place, Monroe
845.782.2249; find them on Facebook

30 Carpenter Place, Monroe
845.783.4466; find them on Facebook

Wally’s Ice Cream Parlor 
846 NY-17M, Monroe 

Museum Village
1010 State Route 17M, Monroe

Jack and Louise Birnberg Preserve
Blooming Grove/Chester

Howland Street, Chester

Rushing Duck Brewing Co.
Battiato Lane, Chester

American House Ice Cream
1 Winkler Pl, Chester
845.469.3174; find them on Facebook

Rustic Wheelhouse
39 Main St, Chester

Clayton Delaneys Dining Saloon
44 Main St, Chester

Trailside Treats Creamery
28 St James Place, Goshen
845.360.5923; find them on Facebook

Joe Fix Its Bicycle Repairs
20 W. Main St, Goshen

Howells & Sunflower Café
27 W. Main St, Goshen 

Craft 47
47 W. Main St, Goshen


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