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Orange County Transportation Council

Greenway Trails/Heritage Tours

Trail of Two Cities 

The Trail of Two Cities is a Hudson River Valley Greenway Trail consisting of approximately twelve (12) miles and connects the City of Newburgh with the City of Beacon in Dutchess County via the Newburgh-Beacon Bridge. Primarily utilizing local streets, the trail loops through portions of the Historic District and allows access to a number of City Parks and known Historic Sites. The trail enters the Town of Newburgh via the Pedestrian sidewalk along the southern side of the bridge. This accesses Grand Street in the Town of Newburgh. Using Grand Street the Trail traverses in a southerly direction for approximately 0.31 miles, entering the City of Newburgh and Leroy Place. Turning right on Leroy Place the Trail makes an immediate left onto Liberty Street. The Trail follows Liberty Street in a southerly direction for approximately 0.09 miles and turns right onto Elmwood Place for approximately 0.17 miles. At the intersection with Powell Avenue the trail traverses a number of side streets for approximately 0.74 miles in a generally southwesterly direction; the Trail turns left onto Powell Avenue, then an immediate right onto Castle Avenue, left onto City Terrace North, then right onto Marne Avenue to the intersection with Carpenter Avenue. The Trail follows Carpenter Avenue in a Southerly direction, turns right onto Gidney Avenue, traversing a generally westerly direction to the intersection of N. Robinson Avenue/US Route 9W. The Trail follows North Robinson Avenue for approximately 0.08 miles, and then enters Downing Park via Mayor Joann Shapiro Drive, traversing in a southeasterly direction for approximately 0.25 miles back to Carpenter Avenue. The Trail turns right onto Carpenter Avenue, then an immediate right onto Third Street, returning back to North Robinson Avenue after approximately 0.20 miles. The Trail continues on North Robinson Avenue for approximately 0.28 miles to the intersection with Broadway. At this point the Trail provided two (2) options; (1) continue in a southerly direction onto South Robinson Avenue for approximately 0.11 miles to the Delano-Hitch Recreational Park or (2) the Trail makes a left turn on to Broadway traversing in an easterly direction for approximately 0.55 miles to the intersection with Liberty Street. At the intersection of Liberty Street, two (2) options are available; (1) the Trail makes a right onto Liberty Street, completing an approximate 0.38 mile loop using Washington Street and South Johnston Street which intersects back to Broadway (2) the Trail makes a left onto Liberty Street, traversing in a northerly direction for approximately 0.81 miles an makes a right onto Broad street for 0ne (1) block. The Trail then changes direction to a southerly direction along Grand Street for approximately 0.66 miles and makes a left turn onto First Street for one (1) block. At this point the Trail offers excellent views to the Hudson River. Changing directions again, back to a northerly direction, the trail continues on Montgomery Street for approximately 0.80 miles to access the intersection of Leroy Place, North Water Street and North Montgomery Street. The Trail turns right onto North Water Street, traversing is a southerly direction for approximately 0.64 miles to the intersection of Fourth Street and Colden Street. The intersection provides two (2) options; (1) the Trail makes a left turn onto Fourth Street to access the Newburgh waterfront along the Hudson River and Unico Park (2) the trail makes a right onto Colden Street continuing is a generally southerly direction for approximately 0.36 miles, where it makes right hand turn onto Broadway for approximately 0.16 miles to Liberty Street. At the intersection of Liberty Street, it is the general end of the Trail and allowing multiple opportunities to traverse the Trail in the reverse direction.

Colonial Terraces Walking Tour 

The Colonial Terraces Walking Tour encompasses the Colonial Terraces neighborhood in the City of Newburgh. The neighborhood was constructed in 1917 to imitate the Garden City Movement in England and used to house the workers of the Newburgh shipyards during World War I. See Map. The Walking Tour is approximately 0.55 miles traversing Thirst Street, Farrell Street, Mckinstry Street, Wilson Street, Bennett Street, Norton Street and Bush Avenue.

Frederick Douglas Trail 

The Frederick Douglass Trail is another Hudson River Valley Greenway Trail, consisting of approximately two (2) miles wholly in the City of Newburgh. The Trail was developed to commemorate the route walked by Frederick Douglass and more than 4, 000 people for the 1870 Jubilee Celebrations of the 15th Amendment to the Constitution. The Trail is a circular loop running the length of South Johnston Street, approximately 0.11 miles, turning left to traverse in a westerly direction along Broadway for approximately 0.63 miles. The Trail then turns left on to Lake Street/NYS Route 32 for approximately 0.13 miles, once again turning left onto Washington Street. The Trail traverses in an easterly direction for approximately 0.68 miles back to South Johnston Street.

Old Town Cemetery - American Revolutionary Walk

Old Town Cemetery – American Revolutionary Walk encompasses the paths within Newburgh’s oldest Cemetery. The cemetery dates back to the early 1700’s and contains nearly fifty (50) American Revolutionary Era burials.

Highlands Falls Trail

The Highland Falls Greenway Trail begins at the West Point Visitor’s Center and winds through the Village of Highlands falls for approximately two (2) miles ending back at the Visitor’s Center, highlighting historic buildings and public parks along Main Street. Beginning at West Point Visitors Center, cross West Point Highway and Main Street. Traverse in a southerly direction along Main Street approximately 0.42 miles to Walnut Avenue. Follow Walnut Avenue in a westerly direction for approximately 0.21 miles to Roe Park. Once the Trial accesses Roe Park there is any number of possibilities to continue on and access main Street/NYS Route 218. The first option is to use Walnut Avenue to gain access to the cemetery towards Dale Ave. A second option if to traverse in a southerly direction along Roe Avenue for approximately 0.14 miles, traverse in a generally easterly direction along Villa Parkway for approximately 0.31 miles. Turn left onto Main Street/NYS Route 218 in northerly direction for approximately 0.22 miles to 0.35 miles, passing Memorial Park. Continue for approximately 0.32 miles, turn right in a easterly direction onto Veteran's Way past Veteran’ Park and the Hostage Monument then left onto West Point Highway ending back at the West Point Visitor’s Center.

West Point Greenway Trail

The West Point Greenway Trail is a loop through the West Point Military Academy that starts at the Thayer Gate near the Village of Highland Falls and the West Point Visitor's Center, ending at the Stony Lonesome Gate near NYS Route 218.

It is recommended to call the Military Police in relation to appropriate attire. Those not in appropriate attire will not be allowed access to West Point.

Fort Montgomery Greenway Trail

The Fort Montgomery Greenway Trail is a linear trail with one endpoint at the Union Cemetery in southern portion of the Village of Highlands Falls. The trail follows Old New York 218 in a generally southern direction for approximately 0.58 miles to the intersection with U.S. Route 9W. The Trail continues in a generally southern direction on U.S. Route 9W through the Hamlet of Fort Montgomery for approximately 1.75 miles to its other endpoint at the Bear Mountain Rotary. From this end of the Trail, the Bear Mountain Bridge can utilized to access Westchester and U.S. Route 9W/U.S. Route 202 can be utilized to access Rockland County.

  • Fort Montgomery Greenway Trail Map

Delaware River Trail

The Delaware River Heritage Trail is approximately six (6) miles in length and owned and operated by the City of Port Jervis; created to allow walkers, hikers, tourists and residents the ability to enjoy the historic sites and river vistas of the City of Port Jervis. See Map. The official start of the Trail is a Fort Decker, located at 127 West Main Street. Using West Main Street the Trails traverses northwest for approximately 0.03 miles. The Trail then turns left onto Ferry Street for approximately 0.1 miles, where it then takes left onto River Road traversing in a south easterly direction, following River Road for approximately 0.38 miles to the intersection of Lumber Street. At this point River Road turns into Water Street, the Trail continues on Water Street for approximately 0.15 miles and turns left onto Pike Street/U.S. Route 6. The Trail continue northeast on Pike Street for approximately 0.06 miles and turns right onto King Street. King Street dead ends at Riverside Park after approximately 0.21 miles. Once in the park, circumvent the ball field to access the existing dike for views of the Delaware River and the High Point monument. In order to continue, the trail loops back to King Street, back to Pike Street, and then turns right in a northeasterly direction through the underpass for approximately 0.17 miles, Following U.S. Route 6. Upon exiting the underpass, the Trail circles to the right following MacArthur Circle and turning left onto Front Street. After approximately 0.18 miles Front Street becomes Jersey Avenue. The Trail continues on Jersey Avenue for approximately 0.71 miles and turns right onto East Main Street/U.S. Route 6. The Trail follows East Main Street for approximately 0.22 miles and turns right onto South Street. Traversing in a northwesterly direction for approximately 0.10 miles, at the intersection with High Street the Trail enters Laurel Grove Cemetery. The Trail follows the Delaware River within the Cemetery, approximately 0.52 miles to the Tri-States Rock in the vicinity of the intersection of the Delaware and Neversink Rivers. Tri-States Rock represents the unifying point of New York, New Jersey and Pennsylvania. The Trail exits the Cemetery along the Neversink River, approximately 0.56 miles at the intersection of East Main Street and South Street. Continuing on East Main Street for approximately 1.26 miles, at some point East Main Street becomes West Main Street, the Trails turns left in a southwesterly direction onto Sussex Street. In approximately 0.10 miles the Trail turn right on to N. Broome Street, passing Orange Square, the Trail turns left onto Pike Street and then a quick right onto W. Broome Street. After approximately 0.11 miles, the Trail turns right onto Canal Street. Using Canal Street the Trail returns to West Main Street after 0.08 miles. Continuing on West Main Street in a north easterly and easterly direction for approximately 0.64 miles, the Trail eventually ends back a Fort Decker.