Ulster County, NY
Launching Oct 15th to 21st 2026. We are please to announce the launch of our new field guide. Learn about Kingston. Woodstock, New Paltz, and more. Explore the Catskills and Hudson Valley, New York on more than a dozen routes.
Introduction
The idyllic and natural characteristics of the Hudson Valley make it a top gravel-bike destination for both New York State and beyond. Situated less than 90 miles from New York City, Ulster County provides access to an exceptional Hudson Valley cycling experience, complete with amenities and hospitality that make any visit to New York’s urban-rural fringe memorable.
More than 100 years of historic conservation and preservation efforts have set the stage for gravel cycling to become one of the premier ways to encounter all that Ulster County has to offer. Rolling hills dotted by grand estates, framed by the rugged mountain landscape, help showcase the county’s leading gravel-cycling-friendly infrastructure. Historic and scenic, Ulster County presents adventurous cyclists with untold days of tranquil exploration.
Since the time of the Revolutionary War, Ulster County has remained an integral part of the national identity of the United States. Gravel rides here connect cyclists to a landscape layered with history—Dutch and British colonial settlements, New York’s original 1777 capital—alongside a thriving arts scene and modern rural lifestyle. Add the picturesque landscape, along with carless accessibility, and riders will quickly see why Ulster County is the Hudson Valley’s premier gravel-bike destination.
Welcome
Ulster County is excited to welcome members of the greater cycling community to the Hudson Valley’s gravel-riding Shangri-La. We’re blessed with breathtaking natural beauty, and proud to share our heritage of conservation. The county offers 1,160 square miles of open space to explore across a variety of seasonal gravel-riding conditions. Ride here, and you’ll be saying, “I love New York Gravel.”
Our rugged mountains provide the perfect backdrop to your Ulster County gravel adventure. Pairing well with the bicycle are a number of historic towns and funky villages possessing unique shops, farm-to-table restaurants, award-winning craft beverages, and dynamic arts scenes. The gravel riding here invites cyclists to wander the countryside, take in the views, and enjoy the wide-open spaces, with amenities that make travel here special.
This edition of the Gravel Adventure Field Guide curates a collection of cycling routes intended to inspire your next gravel-cycling visit to Ulster County. Our destinations center on creative and low-impact ways of seeing the countryside: Pedaling the roads and rail trails will immediately illuminate why the Hudson Valley region is New York’s leading gravel-bike destination.
Road Origins
The first inhabitants of the county were the Esopus, an Algonquian-speaking subgroup of the Lenape (Delaware) people. The Esopus and Warranwankongs were two regional bands residing in the local river valleys and mountains. The Warranko tribe used the Wawarsing Trail to connect settlements on both sides of the Shawangunk Ridge. Their path crossed a steep, eastward-facing rock feature through a natural break near Lake Awosting, before dropping down to the Rondout Creek floodplain. Meanwhile, the Esopus tribe pioneered the Esopus-Minisink Trail, which was likely developed for extensive hunting and foraging activities that followed the lay of the land between the Hudson Valley and Delaware River valley to the west.
Building on Indigenous trail knowledge, the early-arriving European colonists turned these pathways into trade routes. “Old Mine Road,” today’s Route 209, was built directly over the trail that connected Esopus to Minisink; it’s regarded as one of the oldest commercial roadways in the United States. Another road of footpath origins is The King’s Highway. Formed in 1703, it served as the major colonial mail route along the East Coast.
The year 1804 saw the establishment of the Ulster and Delaware Turnpike, often labeled a plank-and-gravel lifeline and known as Route 28 today. This road attracted more settlers into Central New York, resulting in the rise of economic activity. Mills, inns, and forges contributed to the emergence of small hamlet centers, such as Boiceville, Shandaken, Phoenicia, Big Indian, and Pine Hill. Hemlock timber harvesting in the nineteenth century contributed to numerous narrow “bark roads” within the preserved forests of Ulster County—hemlock bark was integral for tanning hides into leather. Eventually, the Ulster and Delaware Turnpike would accommodate the arrival of the railroad.
The railroad enhanced connectivity between the communities of the Hudson River and Catskill Mountains. Five major lines serviced the corridor, providing freight and passenger transportation and kicking off a notable late-nineteenth-century tourism boom. Today, some of this former rail network has been converted into publicly accessible linear parks for hiking, biking, and walking. Beyond its leadership role in New York State’s rail-trail development, Ulster County has added to its cycling infrastructure through the preservation of an unrivaled network of historic carriage roads.
Originally constructed for nineteenth-century horse-drawn carriages, these crushed-stone carriage roads took early tourists across the Shawangunk Mountains outside New Paltz. There are now more than 100 miles of preserved carriage roads for a “car-free” gravel experience. Additionally, these historic carriage roads provide emergency access routes for first responders and act as firebreaks in the event of wildfires. Taken together, the rail trails and carriage roads have helped make Ulster County a major Hudson Valley multiuse trail corridor, one that includes the 750-mile-long Empire State Trail. Running from Albany to New York City, it’s the longest multiuse state trail in the United States.
Communities
Kingston
Woodstock
Woodstock
Settled by Dutch settlers in 1652 as a farming village for trade, Kingston became New York’s first capital in 1777. After the Battle of Saratoga during the Revolutionary War, the city was infamously burned by British forces in October 1777. Since then, Kingston has been divided into distinct historical periods and neighborhoods. It was officially incorporated as a single city in 1872.
In the nineteenth century, Kingston was defined by transportation and canals. It became a major economic hub after natural cement deposits were discovered in 1825. The Delaware and Hudson Canal connected Kingston’s business interests with the coalfields of Pennsylvania. In tandem with cement, river and ocean access led to the manufacturing of bluestone bricks and boats.
Today, Kingston is known for its architectural history and is considered a cultural hub of the Hudson Valley. There are three historic districts—Uptown, Downtown, and Midtown—all listed on the National Register of Historic Places. Art galleries, coffee shops, craft breweries, diverse ethnic food, and a thriving music and nightlife scene give Kingston a vibrant rural-urban aesthetic.
Woodstock
Woodstock
Woodstock
Founded in 1787, Woodstock is a legendary town ensconced within the Catskill Park. Beginning in the 1800s, the town moved toward industrialization, with sawmills and gristmills already operating; the first glass factory opened in 1809. The local economy later got a boost from the quarrying of bluestone as New York City and Philadelphia urbanized.
Much of Woodstock’s notoriety comes from its arts and its counterculture heritage, including being the country’s first arts colony, a hub for the folk-music revival movement (1950s-60s), and the inspiration for the famous 1969 Woodstock Music and Art Fair on a farm 60 miles away. A number of famous musicians, including Bob Dylan and David Bowie, made Woodstock a place to live and work on their art. The community’s historically creative atmosphere continues to draw visitors from around the world, some of whom become residents.
A century-long legacy as a creative sanctuary is why the community has an enduring reputation as a countercultural haven.
New Paltz
Woodstock
Ellenville
The first settlers to arrive in New Paltz were the French-speaking Walloons, who’d fled economic hardship, warfare, and religious persecution in the 1660s and 1670s. New Paltz was chosen as a name to honor the Die Pfalz region in Germany, where the Walloons had most recently found temporary refuge.
Throughout most of the nineteenth century, New Paltz remained a relatively isolated farming community, producing crops, fruit, and wine. In 1828, the halls of higher education arrived when the New Paltz Classical School opened, later becoming today’s State University of New York (SUNY) at New Paltz.
A mixture of natural beauty, hospitable climate, and proximity to the growing cities of the Northeast connected New Paltz with the world at large. New Paltz has evolved into a premier gravel-bike hub within Ulster County due to its seamless car-free linkage between the Wallkill Valley Rail Trail and River-to-Ridge Trail, which directly ties into the historic carriage roads of the Mohonk Preserve and Minnewaska State Park.
Ellenville
Ellenville
Ellenville
Situated at the base of the Shawangunk Mountains, Ellenville grew from a quiet rural community into a prosperous canal town, industrial center, and resort hub. Revitalizing efforts over the decades have positioned the village as an artists’ community and outdoor-recreation gateway.
The industrial era of Ellenville began with the construction of the Delaware and Hudson Canal in the 1820s. This led the village to attract waves of Irish, German, and English immigrants who supported the manufacturing and glassmaking industries. In the mid-twentieth century, the local inventor Joseph Resnick founded Channel Master, a TV antenna factory that employed many locals and marked the town’s peak era of manufacturing.
Today, the village offers a thriving, walkable, and bikeable downtown that continues to serve as a commercial hub centered on arts, culture, and outdoor recreation. An expansion of the Ontario and Western (O&W) Rail Trail in 2024, along with the mountain-bike trail system at Lippman Park, makes Ellenville an attractive bike destination in Ulster County.
Rosendale
Ellenville
Rosendale
Created by the New York State General Assembly on April 26, 1844. The town’s founding was spurred by the arrival of mining during locks construction on the Delaware and Hudson Canal in High Falls, thanks to the discovery of a natural hydraulic cement of high durability.
During its peak in the nineteenth century, local cement production involved 19 large companies and several smaller ventures that, combined, employed over 5,000 workers. Each year, four million barrels of cement were produced—50 percent of the total production of natural cement in the United States.
The cement in the base of the Statue of Liberty and in the Brooklyn Bridge originated in Rosendale. In the 1990s, Rosendale began hosting street festivals that continue to draw crowds, including the Rosendale Street Festival, a weekly farmers market, and live music and cultural events inside the historic Widow Jane Mine.
The Wallkill Valley Rail Trail sparked the renovation of the iconic Rosendale Trestle bridge, a regional landmark on the Empire State Trail with spectacular views.
Sustainable Gravel
Ulster County Gravel Sanctuary An Interconnected Landscape
One reason that Ulster County is a premier gravel-bike destination comes courtesy of the early conservation movement in the United States. The Hudson Valley inspired early environmental advocacy, which in turn led to pioneering government policies and subsequently helped shape how the United States protects its natural resources. This legacy has contributed to a cultural mix of historic preservation, arts, and contemporary community life that now elevates the gravel-cycling experience throughout Ulster County.
The conservation movement began within the ranks of mid-Atlantic educated elites born of families that had made fortunes in resource-extraction industries like logging and mining. By the late 1800s, there was a sense that these natural resources, and the means of extracting them, were at the precipice of collapse. As much as resource extraction had enhanced the country’s economic prosperity, it was also going to lead to its demise unless something was done to curb the excesses of industry.
In New York State, the focus became protecting New York City’s water supply. This resulted in the Catskills becoming designated forest areas with the passing of “Forever Wild” legislation. Drafted in 1885, and adopted and written into the New York State Constitution in 1894, it was an article of protection that set aside approximately three million acres of state-owned land in the Adirondack and Catskill Forest Preserves, forever keeping them as wild forests barred from being sold, leased, or logged. This statute eventually helped to balance large-scale wilderness conservation with outdoor-recreation activities like hiking, paddling, climbing, and gravel cycling.
In parallel, in 1869, the early tourism pioneer Albert Smiley purchased 300 acres, and built a 10-room lodge adjacent to a glacial lake, in the Shawangunk Mountains. His goal was to offer visitors the chance for recreation and renewal of body, mind, and spirit in nature. By the early twentieth century, Smiley had created a carriageway system of roadways, trails, and viewpoints for nature-based guest experiences.
Simultaneously, a rapidly industrializing New York State saw its resort era, with the Catskills transformed into a vibrant vacation hub. East Coast urbanites began traveling to Ulster County for summer entertainment, comedy, dancing, and time in the mountains. These resorts served visitors seeking to escape city life and connect with nature. The resort-era industry included distinct, culturally diverse communities, with two examples being the Borscht Belt and Las Villas.
The Borscht Belt was a flourishing network of Jewish hotels, including the famous Nevele Grand Hotel, and bungalow colonies. Many were founded post-WWII, during a time when Jewish families were excluded from mainstream vacation spots. Alongside the Borscht Belt was Las Villas, centered on the town of Plattekill. Labeled the “Spanish Alps,” Plattekill became the premier destination for the Northeast’s Latino population, especially the New York City Puerto Rican community. During the 1920s, some local Ulster County farmers converted their homes into villas offering Latin music, food, and culture.
During the 1970s, the Hudson Valley continued to lead U.S. conservation efforts. Founded in 1974, the Open Space Institute began as a locally focused land trust that has since expanded its influence across the United States and Canada. It has committed to the protection of open space by partnering with state governments, local municipalities, land trusts of all sizes, and individuals. Altogether, more than 100,000 acres of scenic, natural, and historic landscapes and rail corridors in New York, including Ulster County landmarks like Minnewaska State Park, Wallkill Valley Rail Trail, the Ashokan Rail Trail, and the O&W Rail Trail, have been preserved.
In the twenty-first century, gravel cycling has rapidly moved, within the Hudson Valley’s economy, from a niche-participation sport toward one with a much broader influence on local tourism. Over the coming decades, the legacy of foundational conservation efforts across the last 200 years will continue to cement Ulster County’s role as a leader in gravel-bike-destination development. Here, the synthesis of scenery, culture, rail trails, public lands, small towns, and multiday ride experiences are all part of the blueprint to success.
Get You Free Gravel Guide
Launching Oct 15th to 21st 2026. Distribution takes time. See our Get One link for locations. Learn about Kingston. Woodstock, New Paltz, and explore the Catskills and Hudson Valley, New York on more than a dozen routes.
Hudson Valley Wilderness
The Landscape that defined America
The Hudson Valley region is celebrated for its dramatic river views, fertile agricultural land, and romantically wild mountainous terrain, all epitomized by three natural features in Ulster County: the Hudson River, Shawangunk Ridge, and the Catskill Mountains.
Hudson River
Indigenous groups held different names for the river, but the most well-known originated with the Mohican and Lenape peoples. Muhheakantuck translates to “the river flows both ways,” reflecting the Hudson’s status as a tidal estuary. Twice a day, ocean tides push water upriver past New York City to the Troy Lock and Dam, producing a reverse flow before the waters drop and flow south again.
The river was formed by glacial activity over 20,000 years ago, and its 315 miles of waterway offer the only sea-level break in the Appalachian Mountains. Its convenient access from the Adirondack Mountains to New York Harbor to the Atlantic Ocean initiated its exploration by the Englishman Henry Hudson and subsequent expansion into a nationally important waterway.
Ulster County’s section of the Hudson River offers a dynamic and highly productive state-protected waterway that supports an aquatic ecosystem home to over 200 fish species, including striped bass and endangered sturgeon. In addition to shoreline hiking and biking trails, Ulster County also offers fantastic access to the Hudson River Greenway Water Trail, a network of launch points for motorized boats, kayaks, and stand-up paddleboards.
Shawangunk Ridge
The Shawangunk Mountains, colloquially known as “The Gunks,” comprise a 50-mile-long ridge near New Paltz recognized for its sheer white quartz cliffs. A chain of state parks, preserves, and state forests protect most of the ridge, with Minnewaska State Park Preserve, Mohonk Preserve, Mohonk Mountain House, and the Open Space Institute collaborating to provide public access.
Geologically, the Shawangunk rock is composed of sedimentary conglomerate and sandstone, along with hints of shale.
Quartz gravel and sand from the Appalachian Mountains have been eroding for over 430 million years. These sediments were then deposited by “braided” rivers flowing toward a shallow sea in central to western New York. As the sediment layers thickened, quartz crystalized out of groundwater embedded within the sediments, cementing the gravel and sand together.
The Shawangunks eventually attracted the attention of rock climbers. Unlike other climbing destinations, the Gunks fracture to form ideally featured horizontal cracks, roofs, and airy overhangs, creating exceptionally challenging climbs with massive exposure. Climbing pioneers like Fritz Wiessner and Dr. Hans Kraus established the first routes in the 1930s. As the sport later evolved toward “clean climbing” —a philosophy that eschews the use of rock-damaging pitons—in the 1970s and 1980s, the Gunks became a proving ground for free climbing. With the repeated use of pitons discouraged and a local no-bolt climbing ethic, the Gunks’ prestige only increased. To this day, the Gunks are famed worldwide as a proving ground where climbers earn their routes cerebrally, placing their own removable gear versus relying on in situ protection.
Catskill Mountains Forest Preserves
Integral to Ulster County’s multiple outdoor-recreation opportunities is the Catskill Forest Preserve, part of a 300,000-acre network of state-owned lands designated by the “Forever Wild” legislation. It’s also part of the larger 700,000-acre “Blue Line” of Catskill Park, a proposed boundary the state in 1891 drew on a map using blue ink. All together, the forest preserve showcases spectacular deep forests, waterfalls, and secluded swimming holes.
The progressive “Forever Wild” doctrine fostered Ulster County’s future ability to offer a gravel-bike destination that bridges two distinct ecosystems: the forested, rugged Catskills and the dramatic quartzite cliffs of Shawangunk Ridge, with the latter inhabited by the planet’s only known dwarf pitch pine ridge community. These woodlands consist of pitch pine (Pinus rigida) trees less than 16 feet tall, growing in the thin soils on the flat-topped ridges of quartzite conglomerate.
The forest preserves in Ulster County fall under one of two designations: Wilderness and Wild Forest. Wilderness areas are the more remote and untouched forested areas, with a focus on preserving natural conditions and limiting human presence. Wild Forests, meanwhile, allow for four-season recreational access for gravel and mountain bikers, along with cross-country skiing and snowmobiling in winter. The eastern edge of the county features forest preserves that border the Hudson River, providing stunning views of suspension bridges, tidal flats, and river bluffs.
The Rhythmic Cadence of Ulster County Cycling
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Whether you’re seeking a competitive gravel event or indulging in some self-exploration, Ulster County hosts numerous festivals and events to complement any day of riding. The combination of accessible mixed-surface routes and welcoming communities, along with a calendar of cultural events throughout the year, means cyclists can plan two- to three-day itineraries built around great riding, comfortable overnight stays, enjoyable food stops, and fun festivals.
In addition to local gravel events like the Tour de Kingston and the Shawangunk Grit, there are annual cultural events to build a trip around, including the O+ Festival, Ulster County Fair, Rosendale Street Festival, Woodstock Film Festival, Rosendale International Pickle Festival, and the Woodstock-New Paltz Art & Crafts Fair. It should be noted the pickle festival is so popular it had to leave Rosendale for the county fairgrounds, to accommodate bigger crowds.
The combo of gravel roads and trails, seasonal mountain roads, carriage roads, old farm connectors, and long rail-trail corridors offers adventurous cyclists three distinct landscapes: the Wallkill/Shawangunk side, the central farm-and-hamlet belt, and the Catskills side. The Ulster County cycling experience is about more than pure athleticism; it’s a journey that blends naturalism with modern, minimalist rural living.
To learn more, visit: visitulstercountyny.com/events