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Highland

Hamlet in New York’s Hudson Valley, across the river from Poughkeepsie.

Recommendations

Landmark4.8/5

Walkway Over the Hudson State Historic Park

Poughkeepsie's former railroad bridge now carries walkers and cyclists over the Hudson. The deck stretches more than a mile, with river and valley opening out on both sides, 212 feet above the water.

Culture4.8/5

Franklin D. Roosevelt Presidential Library and Museum

This presidential library and museum follows Franklin and Eleanor Roosevelt through artifacts, photographs, and films from their lives and his presidency. Roosevelt established it as the first presidential library, a model later presidents followed.

Landmark4.7/5

Vanderbilt Mansion National Historic Site

This 54-room Gilded Age mansion holds preserved rooms with original furnishings and works of art. Formal gardens and broad lawns open onto views of the Hudson River.

Stays

Stay4.9/5

The Inn at Kettleboro

Looking for a charming escape in New Paltz? Look no further than The Inn at Kettleboro! Nestled in the heart of NY's stunning countryside, this cozy haven offers quaint rooms with rustic charm and a delicious breakfast spread. With its prime location near hiking trails and local wineries, it's the perfect base for adventure and relaxation.

Stay4.8/5

Saint Hubert's Lodge and Club

This Marlboro bed-and-breakfast shares its grounds with a sporting-clays course. Fifteen stations wind through an old apple orchard, beneath a 70-foot shooting tower.

Stay3/5

Americas Best Value Inn Highland Poughkeepsie

Highland motel with no-frills rooms and breakfast redeemed at a bagel cafe.

Things To Do
Provided by

5/5

7 h

NYC: Train Trip with Sleepy Hollow and Walkway Over Hudson

Our tour begins in the center of Midtown. From Grand Central we will take Metro North up to Tarrytown and Sleepy Hollow. There we will explore this historic area and you will learn about its most famous resident: Washington Irving. Trace the path of Ichabod Crane and the Headless Horseman. We will visit the Old Dutch Burial Ground and Church. After a brief coffee and pastry break, we will take a majestic train ride up to Poughkeepsie where you will be able to experience the new jewel of the river, the Walkway Over the Hudson. We will take a brief elevator ride to the top where you will get incredible views. From there, we will take the train back to the Hudson Highlands where we will visit the charming village of Cold Spring. You will experience views of West Point and the sheer cliffs of Storm King. The tour ends here, but your day need not end- spend the day here or go onto another town!

$135.00

5/5

48 h

Private Hike/Wineries/Walkway Over the Hudson/1 night Hotel

The Walkway Over the Hudson is the longest and highest elevated pedestrian bridge in the world! Benmarl Winery is America's oldest Vineyard! When you accompany two of those facts with a cozy historic town to explore with a plentiful amount of restaurants, bars and eateries, you can't go wrong! Don't feel guilty indulging one bit, because you got some exercise in! Enjoy the famous Walkway Over the Hudson, a moderate to difficult level hike (easier options are available as well), gorgeous hotel accommodations for one night and 2 great local wineries! •the itinerary order is subject to change due to weather and the transportation mode used to arrive in the area. The itinerary change is always in the best interest of our guests. It may be needed (due to availability reasons) to visit different wineries than listed and/or stay at a different hotel.

$1,220.00

5/5

Walkway Over the Hudson & Wineries- Private Transport

The Walkway Over the Hudson is the longest and highest elevated pedestrian bridge in the world! Benmarl Winery is America's oldest Vineyard! When you accompany two of those facts with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! Don't feel guilty indulging one bit at your wineries because you got some exercise in during your amazing time at the Walkway Over the Hudson! Optional bike rentals are available upon request for the Walkway Over the Hudson. Please let us know ahead of time. *Hotel accommodations are available upon request. Simply send us an email and we will be happy to assist you. *Depending on winery availability at the time of your booking, it may be necessary to visit different comparable local wineries than listed. *the Walkway Over the Hudson is a flat paved walkway that is 1.30 miles long. You will get picked up on the other side.

$235.00

4.8/5

1 h 30 mins

Llama/Alpaca Hike and Farm Tour

Your visit begins with a tour of our charming farm, meeting pygora goats, donkeys, sheep, and our famously friendly barn cats, while learning about our historic 1850 homestead on 45 beautiful acres in the Hudson Valley. Next, dive into Llama/Alpaca 101 to discover why these fluffy creatures are the "new unicorns." We’ll cover fun facts, safety tips, and answer questions before starting your trek. Your guided journey takes you through peaceful pastures, paddocks, and by a serene bass pond, with plenty of chances for Llama/Alpaca selfies! This is more than a walk—it's a chance to reconnect with nature, enjoy heartwarming animal encounters, and explore a working fiber farm. Come for the tranquility, stay for the magic!

$70.61

4.6/5

1 h

Alpaca and Llama Trek in Pleasant Valley

You'll laugh, you'll bond, and you might even get a few selfies that'll make your Instagram followers green with envy. Plus, our alpacas and llamas are natural comedians—they’ll keep you entertained with their quirky antics and adorable faces. It's like a live-action comedy show, but with more fluff and less stand-up. So, grab your walking shoes and get ready for a trek that's part nature hike, part comedy tour, and all-around alpaca-awesome! Our farm animals are used to people and love to pose for photos. If you have ever seen our Instagram you know they love to show off. So bring your camera and take some great pictures during it.

$49.00

4.4/5

1 h

Farm Tour at Clover Brooke Llama/Alpaca/Goat Farm

What's So Great About a Farm Tour? Our farm tours focus on education, representation and how to best interact with our animals We take time to teach people about the significance and history of our animals, how to safety and responsibly interact and how we can co-exist with them. Farm tours can help children and adults learn the importance of several farm animals and present them in a new, unique way. After all, how many kids can say they've seen an alpaca or llama? How about meeting mini donkeys and our unique and friendly Pygora Goats ? The Animals On Our Farm Tours When you type "farm tours near me," most tours try to surprise you with ordinary, everyday domestic animals with which you've likely already had an interaction. At Clover Brooke Farm, we provide several unique and vibrant animals that love attention. We want to share with you the journey many of our animals have taken. Each furry (or fuzzy) companion no doubt has a tale to tell.So many very friendly animals to visit.

$21.50

3/5

The Road to Revolution: A Self-Guided Audio Tour in Philadelphia

Are you looking for a way to discover Philadelphia’s Old City without joining a tour group? Explore at your own pace with this self-guided walking tour. • Find out about the individuals who shaped the city from its beginnings to American Independence like Benjamin Franklin and Alexander Hamilton • Hear from producer Reid Addis, a local architect and tour guide • Do it all in 120 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the Voice Map app and enter your code. The app displays directions to the starting point, and when you’re in the right place, pop in your headphones, and just tap start. Voice Map has automatic GPS playback, with turn-by-turn directions. It also works offline.

$14.99

9 h

Wine Tasting Tour To Hudson Valley from New York City

Escape to the scenic vineyards of the Hudson Valley on an exclusive wine tour led by a certified sommelier. This curated experience blends the region's rich winemaking heritage with expert guidance, offering a deeper appreciation of each glass you sip. Highlights: Private Transportation: Relax in comfort as you’re chauffeured from New York City or a local pickup point through the picturesque countryside to renowned Hudson Valley wineries. Expert-Led Tastings: Visit 3 handpicked wineries, where your sommelier will guide tastings, highlighting tasting notes, food pairings, and the winemaking techniques unique to the region. Behind-the-Scenes Access: Enjoy private tours of vineyards and cellars, learning directly from winemakers about their craft, sustainability practices, and the story behind each label. Perfect for wine lovers, weekend explorers, and special celebrations, this sommelier-led journey is a toast to the beauty and flavor of New York's wine country.

$2,895.00

7 h

Fullday London Private tour with Car driver &option:Guide

It is a private customized tour . Client can make itinerary with our guide and visit places in London. It is for minium 1 person & up Private Driver fee & car fee, fuel oil cost are included . 7-8 Hours . can hire also guide in option. Lunch and museum entrances own expense.

$320.00

2 h

Playful Poughkeepsie Scavenger Hunt

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

$21.60

2 h

Nutty New Paltz, NY Scavenger Hunt

$23.20

Hudson Valley Wineries- Private Transport- OR brewery/distillery

Benmarl Winery is America's oldest Vineyard! When you accompany that fact with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! We can't wait to book your reservations, make your itinerary, provide you with transportation (by us or one of our partnered transportation companies). You'll love all 3 of your winery stops for the day! Visit our website for more detailed information. Hotel accommodations are available upon request. Send us an email and we'll be happy to book you in a hotel or a private vacation rental (VRBO or Airbnb). Depending on availability, it may be necessary to visit different comparable local wineries than listed. Whichever winery we choose will also be enjoyable of course! We have lots of wineries in our area. We also can conduct your winery tour in other areas than what's listed such as Dutchess County, Ulster County, Columbia County and or Orange County. Email us for questions.

$235.00

1 h 30 mins

A Spectacular Scavenger Hunt in Marist College

Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!

$14.99

Private Hudson Valley and Estate Tour from NYC with Transfer

Escape the city and uncork the Hudson Valley on a private wine tasting day trip from New York City. Roll through vineyard-draped hillsides and river-carved landscapes that define one of the Northeast's most beloved wine regions. At hand-picked Hudson Valley wineries, enjoy VIP tastings of small-batch, locally crafted wines while learning about the valley's thriving wine culture. Pass by grand historic estates that tell the story of the region's gilded past before pausing at a sweeping Hudson River viewpoint and soaking in scenery that stops you mid-sentence. Travel in comfort from start to finish with a knowledgeable guide bringing the story of New York wine country to life. -VIP tastings at select Hudson Valley wineries with locally sourced food pairings -Scenic Hudson River viewpoint stop - perfect for photos and a breath of fresh air -Small group setting for a more personal and immersive experience -Ideal for couples, friends, and wine lovers looking for a refined day out