Orange County NY attracts over 17 million visitors annually, drawn by shopping, stunning natural beauty, and unique attractions. If you’re visiting Woodbury Common, here are the top 5 destinations that make Orange County a complete Hudson Valley experience—not just a shopping trip.
#1: Woodbury Common Premium Outlets
Annual visitors: 13+ million
Why it’s #1: Not even close—Woodbury draws 10x more visitors than any other Orange County attraction
Why it is Still our Top Pick
This isn’t just New York’s top outlet—it’s a global shopping phenomenon. No other attraction in Orange County comes remotely close to its draw.
The numbers:
- 250+ stores and restaurants (expanded 2024)
- visitors from many countries
- 75% of Orange County’s total tourism
- Visitors from 100+ countries
What makes it irreplaceable:
- Only U.S. outlets for Dior, Loro Piana, Brunello Cucinelli
- Largest luxury outlet collection in North America
- Can’t replicate this experience anywhere else nearby
Bottom line: You’re probably here for this. Everything else on this list is bonus.
Time needed: 4-6 hours minimum
Best day: Tuesday-Thursday to avoid crowds
Start Planning Your Trip to Woodbury Common
#2: LEGOLAND New York Resort
Annual visitors: 1+ million (opened 2021)
Distance: 10 minutes from Woodbury Common
Time needed: Full day (6-8 hours)
Why Families Love It:
Opened in 2021, LEGOLAND quickly became Orange County’s second-biggest draw. This 500-acre theme park is specifically designed for families with kids ages 2-12.
What to expect:
- 50+ rides, shows, and attractions
- 7 themed lands (LEGO City, LEGO Castle, LEGO Ninjago, etc.)
- Miniland: Famous NYC landmarks built from LEGO bricks
- LEGOLAND Hotel on-site
- Seasonal LEGOLAND Water Park
Best for: Families with young children (2-12)
Skip if: No kids or older teens (geared toward younger children)
Admission (2025): $70-100+ depending on season (buy online for discounts)
Season: Late March – early November (weather dependent)
Location: 1 LEGOLAND Boulevard, Goshen, NY 10924
Phone: (888) 690-5346
Insider tip: Combine with Woodbury shopping—LEGOLAND in morning/afternoon, outlets after park closes.
Official website: legoland.com/new-york
#3: Storm King Art Center
Annual visitors: 200,000+
Distance: 20 minutes from Woodbury Common
Time needed: 2-3 hours
Why It’s Iconic:
Storm King is one of the world’s leading outdoor sculpture parks—500 acres of rolling hills showcasing monumental contemporary art. It’s genuinely Instagram-worthy and unlike anything else in the region.
What to expect:
- 100+ large-scale sculptures
- Works by major artists (Alexander Calder, Maya Lin, Andy Goldsworthy)
- Stunning Hudson Valley landscape
- Walking trails throughout
- Tram tours available (seasonal)
Best for: Art lovers, photography, peaceful walks, unique experience
Skip if: Not interested in modern art or outdoor walking
Admission (2025): $20-25 adults, $18 seniors, $12 students, Free for kids under 5
Season: April – November (closed in winter)
Hours: 10 AM – 5:30 PM (Wed-Sun)
Location: 1 Museum Road, New Windsor, NY 12553
Phone: (845) 534-3115
Insider tip: Visit on weekdays for smaller crowds. Bring a picnic (allowed on grounds).
Official website: stormking.org
#4: United States Military Academy at West Point
Annual visitors: 500,000+
Distance: 20 minutes from Woodbury Common
Time needed: 2-4 hours
Why It’s Special:
West Point is America’s oldest military academy (founded 1802) with stunning Hudson River views, rich history, and impressive architecture.
What to see:
- West Point Museum (free) — military artifacts, weapons, uniforms
- Trophy Point — cannons, monuments, river views
- Cadet Chapel — Gothic architecture, largest church organ in Western Hemisphere
- West Point Cemetery — resting place of military heroes
- Campus architecture and parade grounds
Best for: History enthusiasts, patriots, scenic views
Note: Campus tours require advance registration; visitor center and museum are freely accessible
Admission: Museum free; guided tours $15-20 (reserve online)
Hours: Visitor Center 9 AM – 4:45 PM daily
Security: Photo ID required for all visitors 16+; vehicle search
Location: 600 Thayer Road, West Point, NY 10996
Phone: (845) 938-2638
Insider tip: Thayer Hotel on campus has restaurant with Hudson River views—good for lunch.
Official website: westpoint.edu/visiting
#5: Brotherhood Winery & Hudson Valley Wine Trail
Distance: 15-20 minutes from Woodbury Common
Time needed: 2-3 hours (one winery) or full day (wine trail)
Why Visit Brotherhood:
America’s oldest continuously operating winery (since 1839), offering historic underground cellars and award-winning wines.
What to experience:
- Wine tastings ($15-25)
- Underground cellar tours (historic caves from 1800s)
- Beautiful grounds
- Event space and gift shop
Why it’s popular: Combines history, wine, and scenic Hudson Valley setting
Hours: Varies by season (check website)
Tastings: Reservations recommended
Location: 100 Brotherhood Plaza Drive, Washingtonville, NY 10992
Phone: (845) 496-3661
Also Consider: Hudson Valley Wine Trail
Nearby wineries:
- Warwick Valley Winery (hard ciders, bourbon, farm-to-table dining)
- Applewood Winery (fruit wines, oldest farm in Orange County)
- 25+ craft beverage locations in Orange County
Best for: Wine enthusiasts, romantic outings, foodie experiences
Combine with: Warwick village (charming shops, restaurants)