Highland, NY

Highland sits right on the western bank of the Hudson River, offering some of the best outdoor access and river views in Ulster County. The area is best known as the western landing for the Walkway Over the Hudson, a converted railroad bridge that lets walkers and cyclists cross high above the river straight into Poughkeepsie. Right at the bridge's base, you can hop onto the Hudson Valley Rail Trail for miles of paved riding through peaceful woods. Down by the shoreline, Bob Shepard Highland Landing Park provides a quiet spot to relax near the water, while the trails at Franny Reese State Park wind past historic estate ruins up to scenic blufftop overlooks.

ATTRDaniel Case / CC BY-SA 3.0

If you are house hunting here, keep in mind that Highland is an unincorporated hamlet within the Town of Lloyd, which handles municipal zoning, permits, and property records. Homes clustered near the hamlet center generally connect to municipal water and sewer, but properties out in the hills and surrounding farm country rely on private wells and septic systems. The rolling terrain makes for great scenery, though hillside lots and steep driveways call for careful planning around storm runoff and winter snow. If you are hoping to run a short-term rental, be sure to check Lloyd's local codes early, as the town requires permits and limits where vacation rentals can operate.

ATTRJuliancolton / Public domain

Day-to-day life blends small-town routine with easy access to nearby hubs. The historic center around Vineyard Avenue features casual local eateries, service spots, and the town library, while Route 9W and Route 299 host supermarkets, pharmacies, and hardware stores. Apple orchards and farm stands dot the countryside just outside the center, giving the area a distinctly rural feel. When you need more, you are only minutes from the Poughkeepsie train station for direct Metro-North service to New York City, or a short drive west to the vibrant dining and arts scene in New Paltz.