3-day Hudson Valley Adventure Itinerary

The Hudson Valley is an incredible adventure destination filled with a wonderful diversity of state parks, historic elements, and geological phenomenon that will engage your mind and feed your desire for exploration. From the white conglomerate cliffs of the Shawangunks to the historic riverside Gilded Age estates and the fallen remains of ghost towns and mining operations, your journey will take you on an awe-inspiring experience along the shores of the mighty Hudson River and to the birthplace of a nationwide public environmental movement. We’ve put together a three-day itinerary to help you get started and lead you to some of the best locations just north of the hustle and bustle of New York City. There are so many amazing opportunities to choose from, so we’ve listed some of the best locations to help you on your way. You'll find some easy strolls, a couple of relaxing swimming holes, and several heart-pounding climbs, each with their own unique treasures, so follow the route of Henry Hudson, and make your own adventure!

Day 1

Bear Mountain State Park spans 5,205-acres and offers fantastic opportunities for biking, hiking, boating, picnicking, swimming, cross-country skiing, cross-country running, sledding and ice skating. Conceived by George Perkins as a place of “rest and relaxation” from New York City, this park is located on the west side of the Hudson River in Rockland County, New York, and has been enjoyed by millions outdoor enthusiasts since its opening in 1913. You can find a map of Bear Mountain State Park here.

Perkins Tower offers 360-degree views spanning south over Iona Island and West across Harriman State Park. On a clear day you can see over 60 miles to the Manhattan skyline, peaking over the mountain tops to the south. Drive to the top or tackle the half-mile constructed pathway and stairs from the lake. The more adventurous can enjoy the steep and rocky Major Welch Trail.
Bald Mountain is one of the park’s southern mountains with a very steep 1,300-foot ascent along a 3.75-mile there-and-back trail. This "Cornell-Mine Trail" passes the remains of a mining test operation by Thomas Edison and hustles over boulders blasted away from the mountain, eventually leading to the peak which has fantastic lookout to the north and west.
Doodletown is a ghost town at the valley between these peaks. First settled in the 1760s by loggers and miners, it had residents until 1965 when it was abandoned. There are old foundations, roadways, and cemeteries that can still be explored with the help of information signs.
The Bear Mountain Zoo is right across the highway from Hessian Lake! It is on the Revolutionary War base known as Fort Clinton.

Day 2

Hudson Highlands State Park spans nearly 6,000 acres and sits on the eastern side of the Hudson River Valley in Dutchess, Putnam, and Westchester counties. An extensive network of trails, maintained by the New York-New Jersey Trail Conference, traverses the many sections of this park, bringing trekkers from the river’s edge and marshlands to the mountaintops and exposed rock faces. There are historical ruins throughout the property, and each section maintains a unique and special history that is cherished by the Hudson Valley. You can find a map of Hudson Highlands State Park here.

Breakneck Ridge is the most popular trail in the United States east of the Mississippi River, and it is often rated as one of the best day hikes in America. The most popular trail is an approximately 5-mile loop to the summit that rises 1,250 feet within the first three-quarters of a mile!
Mount Taurus (Bull Hill) is not as steep of a climb, but it offers a higher elevation gain on the 2.6-mile Washburn Trail (White) to the summit. Beginning in the days of the American Revolution, these mountains were mined extensively for their iron and copper. Operations continued into the early 20th century, and many of the paths throughout the park are on these former vehicle roads. Results of the excavations are most apparent on the steep quarried rock faces on the south of the ridge.
Mount Beacon is on a separate parcel of land owned by Scenic Hudson, the City of Beacon, and the Town of Fishkill. This section connects to the Hudson Highland’s northern parcel along the Fishkill Ridge and the Overlook Trail. All of these trails connect to the Mount Beacon Fire Tower, which marks the highest summit in the Hudson Highlands.
Denning’s Point, which bends out in the Hudson River, has archeological evidence that may date back to inhabitants from 4,000 years ago. During the American Revolution, Alexander Hamilton penned the first of the Federalist Papers here while visiting an estate. More recently, it operated as one of the more than 130 brickyards in the Hudson Valley until it was left to ruin in 1939.
Bannerman’s Castle, located on Pollepel Island, can be seen from many of the mountaintops and stands as a prominent historical landmark in the heart of the Hudson Valley. While this island has a rich history among Native Americans, Frank Bannerman VI is responsible for building the Scottish-inspired castle between 1901 and 1918. He constructed the building to store and display his military surplus items, a business that brought him much wealth. The island has been vacant except for a few caretakers since an accidental explosion almost 100 years ago, and the castle, while still majestic, continues to deteriorate. Access to the island is only permitted via organized tours. Kayaks and canoes are also available for rental with Hudson River Expeditions.

Day 3

Minnewaska State Park Preserve spans 22,275 acres and offers fantastic opportunities for hiking, mountain biking, boating, picnicking, swimming, cross-country skiing, and trail running. Located on the Shawangunk Ridge in Ulster County, New York, this rocky terrain rises more the 2,000 feet above sea level and hosts 25 miles of footpaths and 35 miles of carriage roads for all levels of skill and enjoyment. It is one of the most popular outdoor destinations in the region, only about a 90-minute drive from New York City. Nicknamed the Gunks, these mountains are renowned among rock climbers throughout the world. An estimated 50,000 climbers visit this region each year, making it one of the busiest rock climbing destinations in America. You can find a map of Minnewaska State Park here.

Lake Minnewaska is a beautiful, family-friendly place to go swimming in the summer. The beach itself is staffed from 11:15 a.m. to 6:45 p.m. throughout the season.
Lake Awosting is a more remote swimming destination in the park that is only accessible by the trails and carriageways. It has a unique, flat rock slab beach that gradually descends into the water. The lake is staffed between 11:00 a.m. and 5:30 p.m.
Millbrook Mountain and Gertrude’s Nose is an approximately 10-mile long loop that gains 850 feet in elevation as it wraps around a stunning white conglomerate cliff edge with incredible views to the north, east, and south throughout the Hudson River Valley.

Mohonk Preserve is comprised of 6,400-acres nestled next to Minnewaska along the Shawangunk Ridge. There are over 70 miles of carriage roads and 40 miles of trails for hiking, cycling, trail running, cross-country skiing, snowshoeing, rock climbing, and horseback riding. Several trails connect this area with Minnewaska; however, their entrances are on opposite sides of the ridge, and you'll probably only have enough time in the day to visit one of these preserves. A map of Mohonk Preserve can be found here.

The Labyrinth and Lemon Squeeze is a 1-mile-long rock scramble that goes under, over, and around gigantic boulders that once crashed down from this prominent, white faced conglomerate cliff side. Your journey will take you up angled ladders, between damp rock slabs, and up a 100-foot rock crevice into the mountain!
Skytop Tower is an internationally renowned landmark of the Hudson Valley. It has open access throughout the year, and there are different types of trails leading up to it depending on the season, your desired activity, and your threshold of adventure.
Mohonk Mountain House is a premiere resort destination. This Victorian castle is a center point of the grounds and a national historic landmark with a world-class restaurant and an award-winning spa.

More points of interest!

We know there are only so many hours in the day, but here are a few more wonderful places to enjoy along your route. The Hudson Valley has so many unique destinations to explore!

Walkway Over The Hudson State Park has become one of the most popular parks and attractions in all of New York State since it’s opening in October 2009. This former train trestle spans 1.28 miles over the Hudson River and stands 212-feet high over water and boat traffic with scenic views north to the Catskill Mountains and south past the Mid-Hudson Bridge to the Hudson Highlands. It is open every day from 7:00 a.m. to sunset and has entrances on its east side at 87 Haviland Road Highland and on its west side at 61 Parker Avenue in Poughkeepsie. Experience the excitement of this historic landmark and explore the Hudson Valley with an unforgettable eagle’s-eye perspective!
Mills-Norrie State Park is comprised of more than 1,000 acres of land that are ideal for walking, jogging, hiking, cycling, cross-country skiing, and snowshoeing. This park treats visitors to exceptional coastal views of the Hudson River, historic elements of the Gilded Age, Mills Mansion tours, and fantastic opportunities for seasonal camping, cabin rentals, and boating.
Vanderbilt Mansion
Home of Franklin D. Roosevelt
Washington's Headquarters
West Point Military Academy

Camping

With all of this day time activity, you’re certainly entitled to try out a local hotel or Bed and Breakfast. However, there are also some great camping locations we want to let you know about:

Rounding out your adventure

The Hudson Valley is renowned for its art and music as well as cider mills and wineries. Treat yourself to some of the very welcoming and energetic social scenes throughout the region. The Falcon, in Marlboro, New York, is an excellent venue in the heart of the region that will warm your heart and soul. It is just one of many gems throughout these vibrant river lands.