Skip to content

Things to do in Highland

Top recommendations from locals

From sightseeing to hidden gems, find out what makes the city unique with the help of the locals who know it best.
Scenic Viewpoint
“One of our region's most iconic spots. Reopened in 2009, this is the world's longest elevated pedestrian bridge and spans 1.28 miles over the Hudson River from Highland to Poughkeepsie. Visitors can bring their dogs, ride bikes, or just talk a casual walk. The bridge also connects the rail trail system between Dutchess and Ulster counties. ”
  • 59 locals recommend
Scenic Viewpoint
“Visit the longest pedestrian bridge span in the world. Bikes rentals available. Incredible sunrises.”
  • 14 locals recommend
Route
“Highest pedestrian walkway. Views of river up and down. miles of hiking and biking trails. ”
  • 8 locals recommend
Grocery or Supermarket
$$
  • 6 locals recommend
Café
$$
“From specialty coffees to rotating taps, Underground is a great place to go. They feature local brewery favorites and a great little menu.”
  • 3 locals recommend
Scenic Viewpoint
  • 4 locals recommend
Scenic Viewpoint
“Renovated railroad bridge for pedestrians to walk over the Hudson. Breathtaking views. ”
  • 4 locals recommend
Bakery
  • 3 locals recommend
Route
“This rail trail starts in Highland, NY and goes all the way over the Hudson Walkway into Poughkeepsie. This rail trail is concrete.”
  • 5 locals recommend
Bar
$$
  • 1 local recommends
Café
$$
  • 2 locals recommend
Park
“Snack bar and small local beach and picnic area. Also have pickle ball court.”
  • 1 local recommends
Food
  • 1 local recommends
Point of Interest
  • 2 locals recommend
Clothes Shop
  • 2 locals recommend

Top restaurants

Café
“From specialty coffees to rotating taps, Underground is a great place to go. They feature local brewery favorites and a great little menu.”
  • 3 locals recommend
Café
  • 2 locals recommend
Bar
  • 1 local recommends
Restaurant
Restaurant
  • 1 local recommends
Japanese Restaurant
Restaurant

Get to know Highland

Explore more on Airbnb

Experiences in Highland