Overview

Welcome to the Hudson Valley. Your guides will meet you at New Paltz Way at 11:00 AM before a 30-minute shuttle to the foothills of the Catskill Mountains, where a signature Trek Travel picnic on the bank of the Ashokan Reservoir and a bike fit await. The ride back to New Paltz winds through quiet country roads lined with historic houses, rolling farmland, and apple orchards, returning you to New Paltz Way with the Shawangunk Ridge rising to the west and the Wallkill River running just below. Once settled in, join your guides for a walking tour of Huguenot Street, one of the oldest continuously inhabited streets in the United States—a row of 17th and 18th century houses that bring colonial America into close focus. This evening, we'll gather for social hour and dinner in a carefully restored 1759 stone house just outside downtown New Paltz.

Overview

From New Paltz, today's route climbs into the Mohonk Preserve, where small roads and carriage paths wind beneath towering cliffs and through dense forest. The Shawangunk Ridge defines the skyline throughout, white quartzite cliffs rising above the tree line in a landscape that draws hikers, climbers, and cyclists in equal measure. After lunch at our favorite café in New Paltz, you'll swap your cycling shoes for trail shoes as you venture into Minnewaska State Park Preserve, where pine barrens, rocky outcroppings, and glacial lakes give way to sweeping vistas across the Hudson Valley and the Catskills. The rest of the afternoon is yours. The village is easy to explore on foot, and the inn’s spa is there if relaxation is the order of the day. Dinner tonight is yours to choose—New Paltz's village restaurants draw directly from the surrounding farms, and the Hudson Valley's farm-to-table culture is well represented here. Your guides can point you toward their favorites.

Overview

Today we leave New Paltz and head north into the heart of the valley. The day's route follows the Empire State Rail Trail before crossing the Hudson River on the Walkway Over the Hudson, 212 feet above the water, with the Catskill Mountains stretching west and the river valley opening in every direction below. Follow quiet Dutchess County roads north to Rhinebeck, a well-preserved village whose tree-lined streets and stone-fronted storefronts have held their character against the decades. Lunch is on your own in the village before settling into Mirbeau Inn & Spa. This evening, a short shuttle takes you to dinner featuring elevated American comfort food with views across the Hudson River.

Overview

Rolling out from Mirbeau Inn & Spa, the morning's roads lead through a patchwork of working farms and open meadows, countryside that feels unchanged by time on the east bank of the Hudson Valley. Midway through the ride, you'll arrive at Greig Farm, a family-run institution in Red Hook that has been welcoming visitors since 1942, where lunch from the season's harvest awaits at their market café. Be sure to pet the resident goats before you head back out on your ride. The afternoon continues through the valley's quieter lanes before returning to Mirbeau. This evening, we'll gather for social hour and a final dinner at Willow, the inn's acclaimed restaurant, raising a glass to new friends and the roads of one of America's most storied landscapes.

Overview

A final morning loop through the rural lanes surrounding Rhinebeck leads into Ferncliff Forest, a 200-acre old-growth preserve of hemlock and hardwood that was once part of the Astor family estate and has been protected as forever-wild land since 1964. Those who prefer a slower start are welcome to linger over a last breakfast at Willow instead. Back at Mirbeau, there's time to shower and check out. At 11:00 AM your guides will shuttle you 30 minutes to the Poughkeepsie train station, where the Hudson Valley gives way to wherever the road takes you next.