Things To Do In Highland, NY: Top 13 Most Unique Spots | Stanton House Inn

United Methodist Church at the corner of Main Street and Vineyard Avenue

Highland, New York, once a quiet, unassuming hamlet of Lloyd, New York, woke up one day to find itself in the limelight. The opening of a $5.4 million visitor center for the Walkway Over the Hudson, a bridge that connects Poughkeepsie and the hamlet, put it on the map. Last year, the walkway was trodden by over 650,000 people, and the visitor center and the eateries nearby saw even more footfall. Highland is a welcome break from the city’s relentless pace. Here, you can hike, bike, and dine to your heart’s content. It’s a place where you can do things, eat places, and attend events, all in the charming setting of Highland.


Ready to explore the best things to do in Highland, NY? Let’s get into it.


Quick hits

  • Explore Highland, NY for a mix of adventure and relaxation
  • From hiking to farm picking, there are plenty of outdoor activities
  • Take in the stunning views of the Hudson River from historic landmarks & parks

A Brief History of Highland, New York

Old photo of the Poughkeepsie-Highland Railroad Bridge

Highland, NY, sits between Poughkeepsie and New Paltz, like a well-loved bookmark in an old novel. It was Anthony Yelverton, a man of vision and enterprise, who first settled here in 1754. He started a ferry service connecting Highland with Poughkeepsie. Yelverton’s Landing, the oldest wooden structure in Highland, still stands on Maple Avenue.


Once a bustling hub where farmers brought their cheese, butter, and livestock to New York City, the riverfront area now hosts the Bob Shepard Highland Landing Park. The hamlet took its name “High Land” from the settlers who sought lands more inland, moving away from the busy, industrial, riverfront. In 1845, Lloyd was officially carved out of New Paltz by the New York State Legislature.


The 1880s and 1890s saw a surge in commerce and passenger travel, thanks to the completion of regional railroads and the Poughkeepsie-Highland Railroad Bridge. Today, that bridge is now the Walkway Over the Hudson.


Be warned, if you’re planning to visit, bring your own set of wheels. Walking may not be the most convenient way to visit all the attractions. Unless all you’re doing is the Walkway Over the Hudson.


Though I assume you wouldn’t be bothering to read this if that was your entire plan.


The Best Things to do in Highland, NY

Residents like to dress up their property and shop for Halloween

Highland, NY offers a variety of outdoor activities including the Walkway Over the Hudson, serene parks like Franny Reese State Park, and outdoor markets in May and October. Activities include apple picking at local orchards, kayaking in Black Creek, swimming in the lake at Berean Park, and hiking at Illinois Mountain and Franny Reese State Park. The town also features farms where you can pick your own fruits and vegetables.


Walkway Over the Hudson

Walkway over the Hudson, from the Highland side

As you amble down the 1.28-mile stretch of the Walkway Over the Hudson, your senses will be regaled by the majestic panorama of the Hudson River. Born in 1889 as the Poughkeepsie-Highland Railroad Bridge, this venerable pedestrian bridge has laughed in the face of time. After a brief hiatus in 1974, it came back to life as a state historic park in 2009.


From dawn ’til dusk, the Walkway stands tall, a beacon to any visitor of Highland. And it’s one of the coolest spot to see some of the best fall foliage near NYC from above, in this writer’s opinion.


And the Hudson Ale Works, a stone’s throw from the Walkway Over the Hudson, is one of the many sprouts that have taken root in Highland in recent times.


Mid Hudson Bridge

Another iconic bridge in Highland is the Mid Hudson Bridge, an architectural marvel that’s been standing since 1930. Designed by engineer Ralph Modjeski, the bridge’s unique tower design and rich history make it a must-see for both history buffs and those who appreciate modern engineering feats.


Franny Reese State Park

Mid-Hudson Bridge

For nature lovers, Franny Reese State Park is a paradise. It offers stunning hiking trails, ancient ruins of former estates, and breathtaking views of the Mid Hudson Bridge and river. Named after Frances ‘Franny’ Reese, a founder of Scenic Hudson, this 251-acre park opened in 2009 and is now maintained by the New York State Office of Parks.

DuBois Farms

If you’re looking to get your hands dirty and enjoy some farm-fresh produce, DuBois Farms is the place to be. This family-owned farm allows visitors to pick their own fruits and vegetables, offering a fun and interactive experience for all ages.

Wilklow Orchards

Another charming agricultural destination in Highland is Wilklow Orchards, where you can pick apples, enjoy fresh produce, and indulge in delicious baked goods. With a history dating back to 1855, this family-run orchard has been delighting visitors for generations.

Johnson-Iorio Memorial Park

If you’re seeking a peaceful retreat by the river, Johnson-Iorio Memorial Park is your haven. Located at 281 Haviland Road, this tranquil riverside park offers stunning views and a serene atmosphere for relaxation.

Bob Shepard Highland Landing

For those who love spending time on the water, Bob Shepard Highland Landing is a hidden gem in Highland. This riverside spot is perfect for boating, fishing, and picnicking along the Hudson River. And it is arguably a hidden gem. This writer has visited the hamlet of Highland, NY, many times, but didn’t discover this spot until researching for this article. It’s definitely off the beaten path.

Hudson Valley Rail Trail

Cycling on the Hudson Valley Rail Trail is a fun October weekend activity with friends

The Hudson Valley Rail Trail, a path stretching 7.1 miles from Highland to well past Lloyd, draws walkers, joggers, and cyclists. Unveiled in 2019, it carves a scenic route from Highland to the Walkway, and onward to the 13-mile Dutchess Rail Trail on the Poughkeepsie side of the Hudson River. Open from the first blush of dawn to the last gasp of dusk, the trail presents a smorgasbord of terrain, from flatlands to uphill battles, making it a splendid way to experience the raw beauty of the Hudson River Valley and maintain your vitality during your Highland visit.


It also goes west, from Highland, NY, all the way to New Paltz and beyond.

Illinois Mountain Park

For a more challenging outdoor adventure, head to Illinois Mountain Park. This beautiful park offers a variety of outdoor activities, including upstate NY hiking trails and panoramic views that are well worth the effort.


Whether you’re an experienced hiker or just looking for a new outdoor challenge, Illinois Mountain Park is a must-visit destination during your stay in Highland.

Shopping & Restaurants in Highland, NY

Highland, NY hosts gastronomic delights along its maing drag. The town is dotted with culinary hotspots like Vigneto Café and Pomo D’Oro. Gunk Haus, a nod to the Shawangunk Ridge, serves up hearty German fare. Lilly Rae In The Hamlet is a cozy corner for boutique shopping and leisurely coffee sipping. Bad Seed Cider Taproom pours out an array of locally brewed ciders, perfect for a tasting tour. Underground Coffee & Ales, a snug cafe and bar, caters to a variety of palates. Hapag Bistro serves up authentic Filipino dishes like Pork Sisig, Bangus Sisig, and Chicken Sisig.


The business district is a bustling hive of bistros, galleries, and cafes, all nestled in buildings that whisper tales of the early 20th century. Studio 89, an art gallery, sports a vibrant mural by local graffiti artist Lady Pink. Knaus Gallery & Wine Bar serves art, pottery, wine, and light meals. The Kiltmaker’s Apprentice, a Highland stalwart, dispatches and rents kilts worldwide via its online portal.

Seasonal Events in Highland, NY

Highland, NY hosts a range of seasonal events and celebrations that display the town’s highlights. Some of the events include:

  • Halloweed Comedy Show
  • Spooky Season Singles Mixer
  • Trippy Costume Party
  • Pumpkin Centerpiece Workshop


There’s always something happening in and around Highland.


And don’t forget about the Christmas events and the New Paltz Winter Carnival! Be sure to check local listings for upcoming events during your visit.

Directions to Highland, New York

Trees lining a scenic road in August

Highland, NY, between New Paltz and Poughkeepsie, is as easy to get to as a cold beer on a hot day. Just a hop, skip, and a jump from Exit 18 on the New York State Thruway. If you’re brave enough to tackle the traffic, you can drive to Midtown Manhattan, though it might take you a couple of hours, or even more if Lady Luck isn’t on your side. If you’re of the train persuasion, you can hitch a ride on the Metro-North line from Poughkeepsie. Or, if you’re in the Big Apple, you can catch a direct line from New York Penn Station to Poughkeepsie Amtrak Station. It’s one of the best train trips from NYC.

Hotels, Inns, and Places to Stay in Highland, NY

Without any traffic, the drive from our Greenwich, Connecticut, bed and breakfast to Highland, New York, takes about an hour and 24 minutes. It’s a beautiful drive up the Hudson Valley.


This writer has only ever visited Highland on a day trip. But if you’d like to stick around a bit longer, check out a few of your options nearby:

Rocking Horse Ranch Resort

For an all-inclusive, family-friendly stay, Rocking Horse Ranch Resort is the ideal choice. This popular resort offers plenty of activities for guests of all ages, including:

  • Horseback riding
  • An indoor water park
  • Live entertainment
  • A variety of outdoor adventures


With so much to see and do, Rocking Horse Ranch Resort is the perfect place to create lasting memories with your loved ones.

Inn at Twaalfskill

The Inn at Twaalfskill is a Victorian gem nestled near the Walkway Over the Hudson. Its spacious rooms, adorned with period Hudson Valley antiques, boast opulent private baths. Common areas with fireplaces invite relaxation, while porches and a patio offer outdoor respite. Amenities include robes, quality bath products, air conditioning, TV, and a gourmet breakfast. Bikes are available for the adventurous.

More Places to Visit Near Highland, NY, in the Hudson Valley

Walk through the old Huguenot area of New Paltz, NY, a beautiful place to wander

Highland’s strategic location in Ulster County provides a wealth of surrounding towns and attractions for exploration during your visit. From the historic Huguenot Street in New Paltz to the cultural attractions of Kingston and the museums and parks of Poughkeepsie, the surrounding area is rich with history and charm.


So why not extend your stay and discover even more of the best things to do that the Hudson Valley has to offer?


New Paltz, NY

Just a short drive from Highland, you’ll find the bustling college town of New Paltz, NY. Here, you can stroll down historic Huguenot Street, visit the Mohonk Preserve, or explore the Wallkill Valley Rail Trail.


Boasting a lively environment and numerous attractions, New Paltz is an essential stop for anyone journeying through the Hudson River Valley.


Kingston, NU

Main street of Kingston

Another nearby town worth exploring is Kingston, New York, the former state capital. Steeped in history and culture, Kingston offers a wealth of attractions, including:

  • The Old Dutch Church
  • Rondout Lighthouse
  • Senate House State Historic Site
  • Hudson River Maritime Museum


Delve into the compelling history and intriguing tales that render Kingston a mesmerizing destination.

Poughkeepsie, NY

The city of Poughkeepsie from the Walkway Over the Hudson

Poughkeepsie, NY, is another nearby city with plenty to offer. Home to Vassar College, Poughkeepsie boasts a variety of museums, parks, and attractions, such as the Walkway Over the Hudson State Historic Park, Locust Grove Estate, and Frances Lehman Loeb Art Center.


Encompassing art and history, Poughkeepsie offers an engaging stop for those keen to discover the Hudson Valley.

Hyde Park, NY

Last but not least, venture to Hyde Park, New York, for a tour of the historic homes and estates of Franklin D. Roosevelt and the Vanderbilt family. Discover the Franklin D. Roosevelt Presidential Library and Museum, Vanderbilt Mansion National Historic Site, and the Culinary Institute of America.


Plunge into the historical richness and grandeur of Hyde Park for a truly memorable experience.


The hamlet of Highland, NY, offers a charming blend of history, outdoor adventures, and local culture that makes it an ideal destination for a memorable getaway. With its prime location in the Hudson River Valley, there’s no shortage of nearby towns and attractions to explore. So why not pack your bags and embark on a journey to discover the best that Highland and its surrounding areas have to offer? Adventure awaits!

Frequently Asked Questions

Is Highland NY a nice place to live?

Highland NY has a lot to offer, with moderately priced homes, parks, and an above-average school system. It’s a great place for families and young professionals who want a suburban feel and moderate political views.

Is Highland NY rural?

Located in Sullivan County and offering convenience in a rural setting, Highland, New York is definitely considered rural. With many retirees living there and most of its residents owning their homes, it’s no surprise that Highland gives off a rural feel.

Is Highland NY a town?

Highland is definitely a town located in Sullivan County, New York, USA with a population of 2,196 according to the 2020 census.

What are the top attractions in Highland, NY?

Highland, NY is home to a plethora of fun attractions, such as the Walkway Over the Hudson, Mid Hudson Bridge, Franny Reese State Park, and DuBois Farms – so come on over for a memorable adventure!

Are there any unique shopping and dining experiences in Highland?

Yes, Highland offers unique shopping and dining experiences! You can enjoy boutique shopping at Lilly Rae In The Hamlet or sample locally crafted ciders at Bad Seed Cider Taproom.

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