This State Has The Best Biking Trail In The Entire World, According To Samantha Brown

Surrounded by majestic maple trees and vintage red barns peppering the rolling hillsides, could there be anything more soothing than a bike ride through Upstate New York? Showcasing the best of Dutchess and Columbia County backdrops, the Harlem Valley Rail Trail is one of the most beautiful bike trails in the U.S. to add to your bucket list and a favorite of travel expert, Samantha Brown. Founded by the Harlem Valley Rail Trail Association in 1996, this 26-mile paved biking path currently runs north-south from Wassaic to Hillsdale (with a current 1-mile gap in the section linking Copake Falls to Hillsdale). The trail has continued to grow slowly but surely throughout eastern New York, with the hope of expanding the trail a total of 46 miles to the village of Chatham. 


Harlem Valley Rail trail! an Idyllic car free 26 miles traveling thru farmlands and forests. See uou on the trail! #cycling #bicycle #harlemvalleyrailtrail #newyork #newyorkstate #newyorkstateofmind #samanthabrow

♬ A Cup of Coffee – Muspace

The Harlem Valley Rail Trail is divided into three paved sections that cut through the heart of Harlem Valley and the Taconic Hills of eastern New York. Worn wooden picket fences border the paved trail, sheltered by a canopy of bright verdant leaves in summer and covered in a thick blanket of fall foliage in autumn. The rural stretches weave past rivers, ranches, and open farmland, showcasing the best of New York's rural, serene wilderness. Historic settlements, a stunning state park, and small, scenic hamlets dot the landscape, creating a picturesque canvas for cyclists and runners/walkers alike. While the trail itself is a stunning ride, Brown suggests bikers also explore off the beaten path and take in the scenic vistas and local landmarks along this region's back country roads. 

Wassaic Station to Coleman Station

While the first portion of the Harlem Valley Rail Trail begins in Wassaic, cyclists can customize their route depending on how far they plan to travel. In fact, about an hour's bike ride west of Wassaic (not on the Rail Trail) is Millbrook Vineyards and Winery, one of Samantha Brown's favorite places. Between the beautiful Catskill Mountains and local fine wines, it isn't hard to see why the vineyard was named "Hudson Valley's flagship winery."

To follow the Harlem Valley Rail Trail north from Wassaic, the first historic town you'll hit is Amenia, which held a prominent place in the steel-making industry, with members playing a critical role of forging weapons for George Washington's Army during the American Revolution. Another lively hot spot in this small New York town, Four Brothers Drive-In is a retro outdoor movie theater that doubles as a restaurant. In addition to daily double features, this old-fashioned cinema offers mini-golf, live music, fire pits, and on-site camping sites for sleeping out under the stars.

After ordering one of Four Brothers' handspun shakes, bike north on the Rail Trail to the historic district of Coleman Station that sits just a 25-minute pedal ride from Amenia. Situated in Dutchess County, Coleman Station was once an operation site of a dairy plant belonging to Sheffield Farms — one of the largest milk-producing farms that distributed dairy throughout New York City in the early- to mid-20th century. 

Millerton to Taconic State Park

Almost 4 miles north from Coleman Station, Millerton is home to a population of under 1,000 residents, but its historic downtown center is buzzing with lively attractions and notable landmarks. Located in the beautiful Hudson Valley, it's no wonder this region made it onto Samantha Brown's list of America's Best Fall Destinations. Ever the quintessential American small town, you'll find everything from local coffee roasters and retro diners to quirky book shops along Millerton's Main Street. Brown recommends visitors pop into Oakhurst Diner, a trendy retro diner on Main Street. It serves all the classic diner comfort foods as well as modern fare, like cobb salad and avocado toast. Afterwards, peruse the shelves of Oblong Books, an independent book shop housed inside an adorable yellow abode. Round out your visit to Millerton at Harney and Sons, another of Brown's local favorites in this village. The flagship tea house sells a vast assortment of teas — the perfect refresher on a hot summer day or warm cozy mug on a chilly fall day.

Roughly 12 miles north from Millerton along the Harlem Valley Rail Trail, Taconic State Park is nestled within the stunning Taconic Mountains in Copake Falls. Consisting of over 6,000 acres, the Iron Works Heritage Trail, Copake Falls, and Rudd Pond are some of the most popular draws within this beautiful New York state park. The park was previously a prolific mining site, and the 1845 Copake Iron Works bears the history of Taconic State Park's mining past, operating today as a public museum.