Things to Do in Highland, NY: A Local Day Out With a Drink Stop

Published October 5, 2026 · By Friend's Corner Tea & Snack Bar · 5 min read

Highland is a small hamlet in the Town of Lloyd in Ulster County, sitting on the west bank of the Hudson River directly across from Poughkeepsie. It is easy to drive through on the way somewhere else, but it is also a great base for a relaxed day out in the Hudson Valley.

From one of the most famous pedestrian bridges in the world to rail trails, farm country and nearby mountain views, here are some of our favorite ways to spend a day in and around Highland, NY, plus the best place on Main Street to refuel with a cold drink.

1. Walk the Walkway Over the Hudson

The number one attraction in Highland is the Walkway Over the Hudson State Historic Park. This former railroad bridge, built in the 1880s, reopened in 2009 as a park for walkers, runners and cyclists. Its deck stands 212 feet above the river and runs 1.28 miles between Highland and Poughkeepsie, making it the longest elevated pedestrian bridge in the world.

The views are spectacular in every season: river traffic below, the Mid-Hudson Bridge to the south and the Catskills and Shawangunk Ridge in the distance. The Highland entrance is on Haviland Road, with parking nearby. Wear comfortable shoes, bring a jacket on breezy days and check the park's website for current hours and events before you go.

Tip: make it a loop

Many visitors combine the Walkway with the pedestrian path on the Mid-Hudson Bridge to make a loop between Highland and Poughkeepsie. It is a great way to see the river from two different bridges.

2. Ride or Stroll the Hudson Valley Rail Trail

The Hudson Valley Rail Trail follows an old railroad right-of-way through the Town of Lloyd and connects to the Walkway at its eastern end. The trail stretches about seven miles through woods, over Black Creek and under stone-arch bridges, linking Highland toward New Paltz. It is part of the statewide Empire State Trail network.

The trail is mostly flat, which makes it a favorite for families, strollers, dog walkers and casual cyclists. It is a peaceful counterpoint to the busy views on the Walkway.

3. Visit Farm Stands and Orchards

The countryside around Highland is part of the Hudson Valley's farm belt, known for apples, stone fruit, berries and vegetables. In season you will find farm stands, orchards and pick-your-own farms in the surrounding towns. Late summer and fall are especially busy, with apple picking, cider and pumpkins. Hours and offerings change with the harvest, so check with individual farms before visiting.

4. Explore New Paltz

A short drive west of Highland, the village of New Paltz is known for its lively main street, shops and restaurants and its college-town energy. History lovers can walk Historic Huguenot Street, where stone houses built by early European settlers still stand. Outdoor lovers head for the dramatic cliffs of the Shawangunk Ridge, where the Mohonk Preserve and Minnewaska State Park Preserve offer hiking, rock climbing and stunning views.

5. Cross the River to Poughkeepsie

Poughkeepsie is right across the Hudson, reachable by car over the Mid-Hudson Bridge or on foot via the Walkway. You can explore its waterfront and riverside parks, then walk or drive back to Highland.

6. Watch the Seasons Change on the River

Highland is a beautiful place to watch the seasons. Spring brings blossoming orchards, summer means long evenings by the river, fall turns the valley into a sea of red and gold, and winter can bring quiet, snowy views from the bridges. The changing light on the Hudson is worth the trip in any month.

Take a Break at Friend's Corner

After a walk across the Walkway or a ride on the rail trail, you will probably be ready for something cold, sweet or warm. Friend's Corner Tea & Snack Bar is at 6 Main Street, near the corner of Main Street and Vineyard Avenue, a short drive from the Highland side of the Walkway.

Here is what we suggest depending on your day:

• After a hot summer walk: a frosty mango or passionfruit smoothie. See our smoothie flavor guide.
• For a taste of something new: a classic Filipino halo-halo or a cold sago gulaman.
• For bubble tea first-timers: try one of the flavors in our first-timer's guide.
• On a cold day: a hot cinnamon or taro milk tea from our winter drink menu.
• Need a pick-me-up for the drive home: a latte or iced americano. Read our coffee guide.

Short on time? Order ahead on our online menu and use curbside pickup. Bubble tea orders should be placed at least 30 minutes in advance. We are closed on Mondays, so plan your visit for Tuesday through Sunday and check our contact page for current hours.

Sample Day Plan

Curious about the Filipino tradition of the afternoon snack break? Read our guide to Filipino merienda.

Tips for Visiting Highland

• Dress in layers. It is often windier and cooler on the bridges than in town.
• Check hours before you go. Parks, farms and small businesses can change hours by season.
• Bring water and sun protection for longer walks and rides in summer.
• Support local. Small businesses on Main Street make the hamlet special.

Make Highland Part of Your Hudson Valley Day

Highland packs a lot into a small area: a world-famous pedestrian bridge, a peaceful rail trail, farm country and easy access to New Paltz and Poughkeepsie. Whatever you choose, end your day with a treat from Friend's Corner Tea & Snack Bar. Stop by Main Street or order online for carryout.