Things to Do in Highland, NY: Walkway, Rail Trail, Riverfront Parks and Restaurants

Things to do in Highland, NY start at the west end of the Walkway Over the Hudson, where Haviland Road meets the 1.25-mile bridge, and spread out from there: the paved Hudson Valley Rail Trail running 7 miles west, two riverfront parks near the Mid-Hudson Bridge, a Route 9W diner that stays open until midnight on weekends, and Walkway At Night on October 24. Highland is a hamlet in the Town of Lloyd, Ulster County, on the west bank of the river across from Poughkeepsie, and it is about 6 miles east of Farmers Choice New Paltz on Route 299. The Walkway's closing time moves twice in October, so check it before you go.

What time does the Walkway Over the Hudson close in October?

Walkway Over the Hudson State Historic Park opens at 7AM every day of the year and closes at sunset, weather permitting. Its 2026 hours table sets the closing time at 6:30PM from October 5 to October 18, 6PM from October 19 to October 31 and 5PM from November 1 through December 31, and the park asks visitors to call 845-834-2867 to confirm hours before a visit. Access is open during operating hours. The Highland approach has a GPS address of 87 Haviland Road, Highland, NY 12528, and the Poughkeepsie approach is 61 Parker Avenue.

Parking on the Highland side is paid. Since January 1, 2025, the Town of Lloyd has charged for parking in all of its lots and marked spaces along Haviland Road, paid at a kiosk or through an app, and Town of Lloyd residents can register their vehicles with the Town Clerk for an exemption. Accessible spaces in the rail trail lot near the caboose are exempt from the charge at all times. The deck is exposed, so bring a layer for the wind over the river. The elevator down to Upper Landing Park on the Poughkeepsie side runs from 9AM until 90 minutes before closing and can stop for maintenance and weather, so confirm it on the elevator hotline, 845-834-3641, before planning a loop around it.

Our page on the dispensary near the Walkway Over the Hudson covers the drive from New Paltz, and the Walkway day trip guide covers which end to start from.

Where does the Hudson Valley Rail Trail start in Highland?

The Hudson Valley Rail Trail starts at the Walkway's west gate and runs 7 miles west across the Town of Lloyd to the town's border at Elting Corners Road, where it connects to the Wallkill Valley Rail Trail, according to Ulster County Tourism. It is a 12-foot-wide asphalt trail, flat or gently sloped, open to walking, running, cycling, inline skating, cross-country skiing and snowshoeing, and with the Walkway and the 13-mile Dutchess County Rail Trail it forms an 18-mile car-free route from Highland to Hopewell Junction.

Parking sits along the whole Highland stretch. The Hudson Valley Rail Trail Association lists the caboose lots at 75 and 100 Haviland Road, which fall inside the Town of Lloyd's paid zone, Commercial Avenue Extension in the hamlet, the Depot at 101 New Paltz Road, Tony Williams Park on South Riverside Road, 589 New Paltz Road, and 650 Route 299 across from Lowe's near the western end. The Town of Lloyd's parks page adds that Tony Williams Park has picnic pavilions and restrooms. Mid-route, the hamlet's Vineyard Avenue sits a block off the trail, which is where the lunch stops below come in. Our Hudson Valley Rail Trail page has the drive from the New Paltz store, about 5 miles to the trail's western end.

Highland's riverfront: two parks under the Mid-Hudson Bridge

Bob Shepard Highland Landing Park, 42 River Road. A 1.7-acre park on the water that the Town of Lloyd bought with Scenic Hudson's help, on the site of a former oil tank farm. It is open year round from sunrise to sunset for walking, picnicking (no fires), fishing and paddling, and it links to the Walkway Loop Trail. Ulster County Tourism lists the park's phone as 845-224-4464.

Franny Reese State Park, 49 Macks Lane. A 251-acre state park that Scenic Hudson conserved and manages, open sunrise to sunset. Its trails follow a historic carriage road past the ruins of a 19th-century estate, and an overlook takes in the Mid-Hudson Bridge and the Walkway from the Highland side. Dogs are welcome on a leash, and a link trail connects the park to the Walkway Loop Trail.

Where can you eat in Highland, NY?

The restaurants on this list sit up the hill from the river, so a meal with the water in view means a picnic table at Highland Landing Park, and a sit-down meal is a few minutes away on Route 9W, Haviland Road or Vineyard Avenue. Each of these leads with food on its own website, and the hours are what each posts there.

Gateway Diner, 3579 Route 9W. A family-owned diner that describes itself as minutes from the Walkway; by road it is about 1.7 miles from the Highland entrance, by OpenStreetMap and OSRM estimates. Breakfast is served all day alongside lunch and dinner. Hours are 7AM to 10PM Monday to Thursday, 7AM to midnight Friday and Saturday and 7AM to 10PM Sunday, and a drive-up window for pickup and delivery stays open until 1AM seven days a week.

Pomo'doro Pizza Cafe, 6 Haviland Road. On the same road as the Walkway's Highland entrance, with pizza that runs from a traditional Grandma pie to Buffalo chicken, from owners who grew up in Italy. Its site posts 10AM to 9PM Sunday to Thursday and 10AM to 9:30PM Friday and Saturday as one block for both of its locations, so call 845-834-3838 to confirm.

El Paso Paso, 78 Vineyard Avenue. A Mexican restaurant in the hamlet with online ordering. Hours are 11AM to 7PM Sunday, 10:30AM to 8:30PM Monday, 11AM to 8:30PM Tuesday to Thursday and 11AM to 9PM Friday and Saturday.

Across the bridge, Poughkeepsie has waterfront dining at the other end of the walk.

Highland events this fall: Walkway At Night on October 24

Walkway At Night runs from 6PM to 7:30PM on Saturday, October 24, 2026. Its ticket page lists both the Highland (west) and Poughkeepsie (east) entrances. The Walkway stays open past its usual 6PM close that week for a moonrise walk 212 feet above the river, and, weather permitting, the Mid-Hudson Astronomical Association sets up telescopes on the deck. Members attend free and non-members pay at the gate or in advance, and the Friends of the Walkway encourage pre-registration to shorten the wait at the gate. Proceeds support the nonprofit's programs and park improvements.

After that weekend the season turns: from November 1 the Walkway closes at 5PM every day through the end of the year, so November and December walks are early-afternoon plans.

The parks' rules, and the drive home

Every stop above is public land, and Walkway Over the Hudson posts plainly that it is a non-smoking park. The state's Office of Cannabis Management puts the vehicle rule just as plainly: "Neither drivers nor passengers can open any cannabis packaging while in a vehicle." Its adult-use page also lists public parks and restaurant patios among the places where using cannabis is illegal. Whatever you buy at the barn rides home sealed, and the New York cannabis laws guide walks through the rest of the rules on where consumption is allowed.

Then Route 299 west to the New Paltz barn

Highland to Farmers Choice New Paltz is about 6 miles and 12 minutes on Route 299, and the barn stands at 1 Old Route 299 beside NYS Thruway Exit 18, so for anyone heading to the highway it is on the way rather than a detour. From the Walkway's Haviland Road lot, our landmark page counts about 7 miles and 13 minutes. Hours are 8AM to 10PM seven days a week, the lot holds about 35 to 37 cars and has EV chargers, and the Highland page spells out the turns. A valid government-issued photo ID that shows you are 21 or older is checked on every visit.

Order Now from the New Paltz menu for pickup: most orders are ready inside an hour. Or Visit Us on the way past.