Hiking & Trails
Hiking & Trails

There’s Something for Everyone in Orange County, NY

Stewart State Forest

New Windsor, 12553

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7,000 acres of wildlife management area with semi-paved lanes for walking, running, mountain biking, horseback riding an...

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Wallkill Valley Loop

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Throughout Orange County 117-mile hiking route that circles the Wallkill River Valley. The trail explores the region by ...

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Walden-Wallkill Rail Trail

Wooster Memorial Park
Walden, 12586

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Built on a former Conrail right-of-way. The rail-trail is open in two sections. The longer, southern section is paved an...

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Storm King State Park

Mountain Rd.
Cornwall-On-Hudson, 12520

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A favorite for avid hikers, this mountain inspired the ecological movement in the United States. Beautiful views of the ...

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Sterling Forest State Park

116 Old Forge Rd.
Tuxedo, 10987

Sterling Forest State Park
Sterling Forest

8-mile Sterling Ridge Trail and 3-mile Allis Trail. 4 mile Indian Hill Loop. 7 miles of Appalachian Trail and 10 miles o...

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Schunnemunk Mountain

Otterkill Rd.
Cornwall, 12553

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Six marked trails ranging from 1.6 to 8.1 miles. Excellent views. Highest point in the lower Hudson Valley (1700 feet).

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Port Jervis Water Shed Trails and Park

1 Skyline Dr.
Port Jervis, 12771

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Beautiful scenery and great trails for biking and hiking. Trails for all levels and abilities with clearly marked areas....

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Pochuck State Forest

County Rt. 1
Pine Island, 10969

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503 acres, no marked trails, but former logging trails, and public access roads. Popular for hunting, hiking, camping, a...

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Outdoor Discovery Center

100 Muser Dr.
Cornwall, 12518

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1 1/2-mile trail designed to study nature. Winds through 4 ecosystems: forest, grasslands, ponds and wetlands. Rotating ...

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Newburgh Waterfront Trail

1 Washington St.
Newburgh, 12550

Newburgh Waterfront Trail
Newburgh Waterfront Trail

Scenic walk along the Hudson River. Picture perfect and peaceful area to sit, walk, or run at. Approximately 1 mile long...

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Huckleberry Ridge State Forest

Hawthorn Blvd.
Greenville, 12771

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500-acre forest. The Shawangunk Ridge Trail hugs the eastern edge of this forest.

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Highlands Trail

Cornwall-on-Hudson, 12520

Highlands Trail
Highlands Trail

A 35-mile trail traversing some of the most beautiful and scenic areas of the rugged highlands region including many par...

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Heritage Trail (paved rail trail)

Goshen, Chester, Middletown & Monroe
Goshen, 10924

Heritage Trail (paved rail trail)
Heritage Trail

Converted rail bed of the Erie Railroad. Walk, jog and bike on this 18-mile scenic route. Trail entrances in Goshen, Che...

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Delaware River Heritage Trail

127 Main St.
Port Jervis, 12771

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A 6-mile trail created to allow walkers to enjoy the city’s historic sites and river vistas that have been immorta...

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Crows Nest

Route 9W South of Storm King Mountain
Cornwall, 12518

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No marked trails, faint paths, beautiful views.

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Black Rock Forest

Rt. 9W
Cornwall, 12518

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Northwest of West Point, marked and unmarked trails ranging from short walks to long hikes. Fires, bathing and camping p...

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Back Track Inn

92 Rt. 284
Unionville, 10988

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4 bunks available only to hikers on the Appalachian Trail. Late Apr-early Nov. Post office is drop point for Trail trave...

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Appalachian Trail

Orange Tpk.
Southfields, 10975

Appalachian Trail
Appalachian Trail

Spanning from the New Jersey border to the Hudson River (about 35 miles), the trail was founded here in 1923. A lengthy ...

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Wine and Dine: Truffles Galore! A Chef's Brunch + Wine Tasting Event @ City Winery
29 Jan    
12:00 pm-3:00 pm
City Winery Hudson Valley invites you to a very special Brunch & Wine Tasting focused on the glorious Truffle! Doors open at 12:00 PM and [...]
Bonsai Bar @ Newburgh Brewing
29 Jan    
1:00 pm-3:00 pm
Grab your friends, grab a drink and come make tiny trees with us! We’re bringing the awesome art of bonsai out of the hedged in [...]
Music Bingo Mondays @ DUBCO
30 Jan    
6:00 pm-8:00 pm
Come join us for an amazing night of music, prizes, and drink specials. It's Music Bingo @ Destination Unknown Beer Company! Test your music knowledge [...]
30 Jan
30 Jan    
7:30 pm
Every Monday in Middletown Team sign-ups start at 7:30pm, first game starts at 8pm. Winning team will receive "Pizza E Birra Bucks" and will sign [...]
01 Feb
Featuring William Pearson! Join us on Wednesday evenings on the patio for our Wine Down Wednesday music and wine series! Free to attend, the series [...]
01 Feb
01 Feb    
6:30 pm-7:45 pm
From Colonial Times to Present with Dr. Myra Armstead - In observance of Black History Month please join us for a special lecture. This lecture [...]
Big Dogs Brewery Grand Opening Weekend
02 Feb    
3:00 pm-10:00 pm
Formerly The Brewery at Orange County HOPS  
Anders Osborne Solo Acoustic featuring Jonathan Sloane @ City Winery
City Winery Hudson Valley Presents Anders Osborne solo acoustic, live in concert on Thursday, February 2nd, at 8 PM At one point on his 2019 album, [...]
Live Music @ Tin Barn Brewing
03 Feb    
6:00 pm-9:00 pm
1/27 - The Harrison's 6-9pm 1/29 - Black Cat Bone 2-5pm 2/3 - The Mugshot's 6-9pm 2/5 - OC5 2-5pm 2/10 - Hudson Blue 6-9pm [...]
Blues Invitational @ DUBCO with the TeeVee Allstars
03 Feb    
6:30 pm-9:30 pm
Everyone's favorite Blues Jam now happens every other week at the fabulous DUBCO Acres (that's Destination Unknown Brewing Company) which recently opened its new location [...]
Big Dogs Brewery Grand Opening Weekend
03 Feb    
7:00 pm-10:00 pm
Formerly The Brewery at Orange County HOPS  
Drowned Lands Cabin Fever Winter Festival
February 4th & 5th Outdoor Ice Bar, Pastry Stouts, Firepits, Sledding Snow Shoes, Winter Cocktails & Hot Toddies. Food Trucks & Live Music Tickets below
Long Lot Brewery's 5th Anniversary Celebration
We’d like to invite you and your friends to join us at the farm as we celebrate our fifth anniversary! Not only will we have [...]
Live Music at Angry Orchard: Ryan Leddick
04 Feb    
4:00 pm-7:00 pm
Join us at the Cider House on February 4th to enjoy live music from Ryan Leddick. Grab a seat in our taproom, order a pint [...]
Drowned Lands Cabin Fever Winter Festival
February 4th & 5th Outdoor Ice Bar, Pastry Stouts, Firepits, Sledding Snow Shoes, Winter Cocktails & Hot Toddies. Food Trucks & Live Music Tickets below
Jazz Brunch at The Cove
05 Feb    
12:30 pm-3:30 pm
Sunday Jazz Brunch at The Cove featuring jazz artists from the area. Feb 5- Mitch Schecter Trio with John Arbo and Steve Rubin Feb 12 [...]
05 Feb
05 Feb    
1:00 pm-3:30 pm
ADVANCE REGISTRATION IS MANDATORY FOR ALL PROGRAMS. PLEASE CALL THE PARK  TO REGISTER. All events will meet at the Visitor’s Center unless otherwise noted. For [...]
Music Bingo Mondays @ DUBCO
06 Feb    
6:00 pm-8:00 pm
Come join us for an amazing night of music, prizes, and drink specials. It's Music Bingo @ Destination Unknown Beer Company! Test your music knowledge [...]
06 Feb
06 Feb    
7:30 pm
Every Monday in Middletown Team sign-ups start at 7:30pm, first game starts at 8pm. Winning team will receive "Pizza E Birra Bucks" and will sign [...]
08 Feb
Featuring Vito Petrocito Join us on Wednesday evenings on the patio for our Wine Down Wednesday music and wine series! Free to attend, the series features [...]
08 Feb
City Winery Hudson Valley presents Denny Laine – ‘Acoustic Songs and Stories’ live in concert on Wednesday, February 8 at 8 PM, doors open at [...]
Denny Laine - 'Acoustic Songs and Stories' @ City Winery
City Winery Hudson Valley presents Denny Laine – ‘Acoustic Songs and Stories’ live in concert on Wednesday, February 8 at 8 PM. Denny Laine is [...]
Puppies & Pinot @ City Winery
Treat your best furry friend to dinner out.  Dine with fellow animal lovers in our Falls Room or outdoor patio (weather permitting), with your human [...]
Ladies Night Winter Market Shop & Dine
09 Feb    
5:00 pm-9:00 pm
Ladies Night Winter Market 10+ vendors ~ $10 admission and a champagne cocktail ~ Complimentary admission with dinner Don’t miss our Valentine’s weekend shopping and [...]
09 Feb
09 Feb    
6:00 pm-9:00 pm
Need to Know: Doors open at 5:45 PM and event begins at 6:00 PM. Must be 21 years of age. All sales are final. Allergens: [...]
Angry Orchard Trivia Night: New Girl Edition
10 Feb    
5:00 pm-8:00 pm
Join us for New Girl trivia! Arrive by 5pm to register your team (first come first serve), choose from a variety of exclusive hard ciders [...]
Live Music @ Tin Barn Brewing
10 Feb    
6:00 pm-9:00 pm
1/27 - The Harrison's 6-9pm 1/29 - Black Cat Bone 2-5pm 2/3 - The Mugshot's 6-9pm 2/5 - OC5 2-5pm 2/10 - Hudson Blue 6-9pm [...]
11 Feb
The “Arts Builds Confidence” Student Showcase hosted by the Orange County Arts Council has been a yearly tradition at Galleria at Crystal Run. For the [...]
Valentine's Weekend
11 Feb    
11:00 am-5:00 pm
Valentine’s Weekend • Tour & Tasting • Feb. 11 & 12 $60 per couple Enjoy two locally made cupcakes from Bakery Plus, a family run [...]
Valentine Craft Market
11 Feb    
11:00 am-5:00 pm
Come Drink, Shop and Enjoy at Tin Barn Brewing
Galentines Brunch @ The Venue at Winding Hills Golf Club
Tickets are now available for our Galentine's Brunch! Seatings are 10:00am and 12:30pm. Send an email to events@windinghillsgc.com with your name and the total number [...]
Superb Owl Party @ Hudson Highlands Nature Museum
Join Nature Educators and our MVO Gus the Screech Owl who will quarterback your morning program! Learn all about our amazing local owls and meet [...]
Valentine's Weekend
12 Feb    
11:00 am-5:00 pm
Valentine’s Weekend • Tour & Tasting • Feb. 11 & 12 $60 per couple Enjoy two locally made cupcakes from Bakery Plus, a family run [...]
Music Bingo Mondays @ DUBCO
13 Feb    
6:00 pm-8:00 pm
Come join us for an amazing night of music, prizes, and drink specials. It's Music Bingo @ Destination Unknown Beer Company! Test your music knowledge [...]
13 Feb
13 Feb    
7:30 pm
Every Monday in Middletown Team sign-ups start at 7:30pm, first game starts at 8pm. Winning team will receive "Pizza E Birra Bucks" and will sign [...]
Valentine's Day Dinner Party
14 Feb    
2:00 pm-8:00 pm
Join us on Tuesday, February 14 for a Valentine’s Day dinner! Our chef has created a special menu - $70 per person
Valentine's Day Dinner
14 Feb    
5:00 pm-8:00 pm
We will be open for dinner on Valentine’ Day. Come enjoy our Winter Menu with Valentine’s Dinner Specials. RESERVE ONLINE OR CALL FOR TAKE-OUT OR [...]
Sip, Paint, Love - A Bubbles & Brushes Special Event
Love is in the Air and on the Canvas! Vicki Andrade from ArtVicki is back to draw out your inner Picasso through expert tutelage as [...]
15 Feb
Featuring Callie Mackenzie! Join us on Wednesday evenings indoors in The Falls Room for our Wine Down Wednesday music and wine series! Free to attend, [...]
15 Feb
15 Feb    
5:00 pm-11:00 pm
Come enjoy and instructed paint and sip class with your galentines at the Sugar Shack Factory. Includes wine, finger foods, and painting materials
Angry Orchard Open Mic Night
16 Feb    
6:00 pm-8:00 pm
Join us at the Cider House for Open Mic Night! Event is 18+. No cover. Take advantage of Angry Hour and enjoy $1 off your [...]
Winter Dining Event - Presidents Weekend
17 Feb    
6:00 pm
Join us for our Winter Dining Event over Presidents Weekend! The evening begins at 6:00, socializing with Cocktails and Hors d'oeuvres. Guests are then ushered [...]
Blues Invitational @ DUBCO with the TeeVee Allstars
17 Feb    
6:30 pm-9:30 pm
Everyone's favorite Blues Jam now happens every other week at the fabulous DUBCO Acres (that's Destination Unknown Brewing Company) which recently opened its new location [...]
Maple Sugar Tours 2023 @ Hudson Highland Nature Museum
As winter winds down, it’s maple sugaring time! Visit us to see, learn, and TASTE! Learn how to identify and tap sugar maple trees, discover [...]
Strawberry Fields: Ultimate Beatles Brunch @ City Winery
City Winery Hudson Valley presents Strawberry Fields: Ultimate Beatles Brunch - President's Day Weekend! live on Saturday, February 18th at 12 PM. GRATUITY NOT INCLUDED IN TICKET [...]
Westtown Brew Works "On Ice"
Westtown Brew Works “On Ice” (aka Ice Fest) is back in full form this year! And with new additions…yes there will be FIRE! We will [...]
Washington's Birthday Celebration at Knox's Headquarters
Tours of the house Sunday February 19 at 10:00 AM, 11:00 AM, 12:00 PM, 1:00 PM, 2:00 PM & 3:00 PM. Quill and ink writing [...]
Maple Sugar Tours 2023 @ Hudson Highland Nature Museum
As winter winds down, it’s maple sugaring time! Visit us to see, learn, and TASTE! Learn how to identify and tap sugar maple trees, discover [...]
Jazz Brunch at The Cove
19 Feb    
12:30 pm-3:30 pm
Sunday Jazz Brunch at The Cove featuring jazz artists from the area. Feb 5- Mitch Schecter Trio with John Arbo and Steve Rubin Feb 12 [...]
Music Bingo Mondays @ DUBCO
20 Feb    
6:00 pm-8:00 pm
Come join us for an amazing night of music, prizes, and drink specials. It's Music Bingo @ Destination Unknown Beer Company! Test your music knowledge [...]
20 Feb
20 Feb    
7:30 pm
Every Monday in Middletown Team sign-ups start at 7:30pm, first game starts at 8pm. Winning team will receive "Pizza E Birra Bucks" and will sign [...]
22 Feb
Featuring Ethan Klee! Join us on Wednesday evenings indoors in The Falls Room for our Wine Down Wednesday music and wine series! Free to attend, [...]
23 Feb
23 Feb    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
24 Feb
24 Feb    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
24 Feb
24 Feb    
6:00 pm-9:00 pm
City Winery Hudson Valley invites you to join us at our Wine and Dine Series featuring a four-course Mediterranean tasting menu. Doors open at 5:45 [...]
24 Feb
West Point's Winter Culinary Event of The Year: Join us for our Whiskey pairing dinner/tasting event featuring Whiskey, Bourbon, and Scotch presented by Diageo Representatives. [...]
25 Feb
25 Feb    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
Wassail Winter Fest at Angry Orchard
25 Feb    
5:00 pm-9:00 pm
Join us for our annual Wassail Winter Fest! Celebrate this traditional English holiday with live music, outdoor games, food trucks, the release of our Wassail [...]
Croce Plays Croce @ SLPAC
OME Presents, Croce Plays Croce at Sugar Loaf Performing Arts Center in Chester, NY.  A.J. Croce performs Croce Plays Croce, a special night of music [...]
26 Feb
26 Feb    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
Maple Sugar Tours 2023 @ Hudson Highland Nature Museum
As winter winds down, it’s maple sugaring time! Visit us to see, learn, and TASTE! Learn how to identify and tap sugar maple trees, discover [...]
Jazz Brunch at The Cove
26 Feb    
12:30 pm-3:30 pm
Sunday Jazz Brunch at The Cove featuring jazz artists from the area. Feb 5- Mitch Schecter Trio with John Arbo and Steve Rubin Feb 12 [...]
27 Feb
27 Feb    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
Music Bingo Mondays @ DUBCO
27 Feb    
6:00 pm-8:00 pm
Come join us for an amazing night of music, prizes, and drink specials. It's Music Bingo @ Destination Unknown Beer Company! Test your music knowledge [...]
27 Feb
27 Feb    
7:30 pm
Every Monday in Middletown Team sign-ups start at 7:30pm, first game starts at 8pm. Winning team will receive "Pizza E Birra Bucks" and will sign [...]
28 Feb
28 Feb    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
01 Mar
01 Mar    
9:00 am-5:00 pm
This February, join us for our second “Foundry Flea” event! This ONE TIME sale will provide you with AMAZING DEALS on old, antique, vintage, and/or [...]
03 Mar
In a career that has already spanned a half-century, Jorma Kaukonen has been one of the most highly respected interpreters of American roots music, blues, [...]
Maple Sugar Tours 2023 @ Hudson Highland Nature Museum
As winter winds down, it’s maple sugaring time! Visit us to see, learn, and TASTE! Learn how to identify and tap sugar maple trees, discover [...]
Top O' the Mournin': Murder Mystery Dinner @ Brotherhood, America's Oldest Winery
04 Mar    
7:00 pm-11:00 pm
D.O.A Mysteries presents Top O’ the Mournin’ Poor old Seamus has passed away and everyone’s gathered at his wake to say goodbye. But soon mourning [...]
Events on 30 Jan
Music Bingo Mondays @ DUBCO
30 Jan 23
Warwick
30 Jan
Events on 01 Feb
Events on 06 Feb
Music Bingo Mondays @ DUBCO
6 Feb 23
Warwick
06 Feb
Events on 11 Feb
Valentine's Weekend
11 Feb 23
Washingtonville
Valentine Craft Market
11 Feb 23
Sugar Loaf
Events on 12 Feb
Events on 13 Feb
Music Bingo Mondays @ DUBCO
13 Feb 23
Warwick
13 Feb
Events on 14 Feb
Events on 15 Feb
15 Feb
15 Feb 23
Middletown
Events on 16 Feb
Angry Orchard Open Mic Night
16 Feb 23
Walden
Events on 20 Feb
Music Bingo Mondays @ DUBCO
20 Feb 23
Warwick
20 Feb
Events on 22 Feb
22 Feb
Events on 23 Feb
23 Feb
23 Feb 23
Port Jervis
Events on 24 Feb
24 Feb
24 Feb 23
Port Jervis
24 Feb
Events on 25 Feb
25 Feb
25 Feb 23
Port Jervis
Croce Plays Croce @ SLPAC
25 Feb 23
Sugar Loaf
Events on 26 Feb
26 Feb
26 Feb 23
Port Jervis
Jazz Brunch at The Cove
26 Feb 23
Lake
Events on 27 Feb
27 Feb
27 Feb 23
Port Jervis
Music Bingo Mondays @ DUBCO
27 Feb 23
Warwick
27 Feb
Events on 28 Feb
28 Feb
28 Feb 23
Port Jervis
Events on 01 Mar
01 Mar
1 Mar 23
Port Jervis
Events on 03 Mar
03 Mar

Book Your Stay In Orange County, NY

Sleep in an architecturally significant B&B, or book a room at a nationally known hotel. Casual travelers as well as visitors looking for luxury will find a wide range of properties to consider. There are lodging options for everyone – Try our user-friendly lodging search below and come stay with us in Orange County, NY.