Hudson Valley Biking 8 Days

Beacon

Arrive to charming Beacon, a town on the Hudson River that has been enjoying a ‘refresh’. Stay at the Roundhouse, a unique, historic property overlooking a beautiful waterfall in the center of town. The property includes several masterfully restored buildings. There’s also a restaurant with a wide patio above the water, a stylish bar with a fireplace and an in-house yoga studio. Visit DIA Beacon, the quirky art museum along the waterfront or, take a warm-up ride and stop at one of the craft breweries in town.

Marlboro & Milton

From Beacon, ride out of town and cross the Hudson River on a bike lane before turning north along the river. Stop and visit Benmarl Winery, who lays claim to be the oldest vineyard in America. Have lunch in the delightful village of Marlboro. Late afternoon, pass through Milton and then just before the hotel, pop into Locust Grove farm, or the brewery next door for a wee pint. Settle into the Buttermilk Falls Inn & Spa, set on a 75-acre estate. Enjoy dinner at Henry’s at the Farm.

Ride distance: 20mi (30km); elevation gain 1,300’ (430m) or 30mi (50km); gain 2,350’ (780m).

Ulster County & New Paltz

Ride west into Ulster County to the historic town of New Paltz, surrounded by nature preserves and anchored by a state university. NY Times describes New Paltz as: “sporty, brainy, cultured, and beautiful. Cradled by a mountain range, surrounded by meadows and forested preserves cut through by a river, and specked with historic houses, shops and galleries.” On Huguenot Street, seven original stone houses are part of a 10-acre historic district and museum. It’s also a great spot for lunch – a new bakery recently opened that specializes in cheesecake that we can heartily recommend. If you are a craft beer enthusiast, visit the New Paltz Brewing Company. For dinner, venture out to the Falcon in nearby Marlboro for dinner and world-class live music.

Ride distance: 31mi (50km); elevation gain 1,770’ (590m) or 51mi (83km); gain 3,300’ (1,100m).

Rhinebeck

Ride north and cross the Hudson on the remarkable walkway/bikeway over the Hudson; enjoy the view as you cycle across the longest elevated pedestrian bridge in North America. Cycle past the Culinary Institute of America which takes advantage of its location with the abundance of nearby farms and vineyards. Restaurant options at the Institute grounds including the Bocuse Restaurant, named after the Lyonnaise chef Paul Bocuse and which boasts an airy, bistro-style interior with a French menu that includes menu items from Paul’s first restaurant. Further north, visit the Franklin Roosevelt Museum and the Vanderbilt Mansion, a National Historic Site (there are 263 properties and districts listed in Dutchess County alone). Arrive to Rhinebeck, settled by the Dutch in the 1680’s. Peek in the Beekman Arms which has operated continuously since 1766, retaining much of its colonial charm and character. Check out the Antique Market, a multi-dealer antique emporium that is located behind the hotel in a classic 2 story barn and visit the eclectic shops that make up Montgomery Row. Stay at the Mirbeau Inn & Spa, which opened in 2019, and is reminiscent of a French chateau.

Ride distance: 31mi (50km); elevation gain 1,335’ (445m).

Redhook, Woodstock & Hudson

There are several ride options today. Cross the Hudson on a bike lane over the Kingston-Rhinecliff bridge to the iconic village of Woodstock with an option to pass by the Ashokan Reservoir, one of New York City’s pristine water sources. An alternate ride stays on the east side of the river and loops through the charming village of Red Hook. A metric century option reaches the river’s namesake village of Hudson. Back in Rhinebeck, visit the one of the largest collections of early airplanes in the world at the Old Rhinebeck Aerodrome. Dine out at one of the town’s popular restaurants.

Ride distance: 27mi (44km); elevation gain 1,200’ (400m) or 44mi (72km); gain 2,280’ (760m) or 60mi (100km); gain 1,380’ (460m).

Troutbeck

Ride from Rhinebeck east through more of Dutchess County. Stop at a cool café/grocer for a mid-morning coffee and then continue through horse farm country to the village of Stanford, which has good lunch options. Visit Millbrook Vineyards on the Dutchess Wine Trail where you can taste Cabernet Franc, Chardonnay, Pinot Noir or Tocai Friulano. Or, if a late afternoon ice-cream is more tempting, you’ll pass by an option in Amenia, the nearest village to the Troutbeck Inn. This idyllic property sits on 250 acres so you’ll have a peaceful retreat. Play tennis, go for a swim or tuck into a book in the comfortable library reading room before dinner in the acclaimed restaurant.

Ride distance: 20 mi (33km); elevation gain 1,020’ (340m) or 31 mi (50km); gain 1,950’ (650m) or 38 mi (61km); gain 2,100’ (700m).

Millerton & / or the Housatonic River Valley in CT

We have several options for you to consider on this day. Ride the Harlem Valley Trail to Millerton, voted one of America’s Favourite Small Towns. Stop in at Irving Farm for a fresh roasted coffee and then visit any one of the many art galleries and antique stores. On the return route, stop in at an organic farm market and sample some of the owners pickled, baked, jammed, stewed and simmered bounty. Or consider a loop into Connecticut and the Housatonic River Valley. Near a trailhead for the Appalachian Trail, cross a historic covered bridge built in 1842 and now a National Historic Monument. Pass historic barns on quiet secondary roads to Kent, a charming village with great restaurant options for lunch before riding back to Troutbeck. Arriving back to the hotel, relax and enjoy another dinner in the delightful dining room.

Ride distance: 20mi (32km); elevation gain 1,000’ (340m) or 36mi (60km); gain 2,700’ (900m).

Departure Day

Depart at your leisure. The station at Wassaic is easily reached by taxi.