Most visitors to Woodbury Common Outlet don’t realize Orange County sits in the heart of the Hudson Valley—one of New York’s most scenic regions. After helping thousands of shoppers plan their trips since 2014, we’ve learned that extending your stay by even one day transforms a shopping trip into a proper Hudson Valley experience.
This guide covers everything within 30 minutes of the outlet, tested and verified during multiple visits throughout 2024-2025. Distances and times are from Woodbury Common’s main entrance.
Plan Your Day: Quick Reference
Nature lovers: Bear Mountain (15 min) + Storm King Art Center (25 min)
Wine enthusiasts: Brotherhood Winery (20 min) + Warwick Valley (15 min)
History buffs: West Point (20 min) + Museum Village (15 min)
Families: Trailside Zoo (15 min) + Bear Mountain activities
More shopping: Crystal Run Mall (20 min) + Sugar Loaf artisan village (30 min)
Parks & Outdoor Recreation
Bear Mountain State Park
15 minutes north via NY-17
Bear Mountain consistently ranks as the Hudson Valley’s most visited park, drawing over 5 million annual visitors to its 5,205 acres. The park sits where the Hudson River cuts through the mountains, creating dramatic elevation changes and river views.
Peak activities by season:
- Spring-Fall: Perkins Memorial Tower hike (moderate, 2 miles round trip). The 360-degree views from the top include seven states on clear days. Arrive before 10am on weekends to avoid parking issues.
- Summer: Hessian Lake swimming beach and pedal boat rentals ($20/hour). The beach gets crowded after noon on hot days.
- Winter: Outdoor ice rink (weekends December-February, weather permitting). Skate rental $8, admission $5. Much less crowded than NYC rinks.
Parking reality: Free but limited. Lots fill by 11am on sunny weekends. Overflow parking adds a 10-minute walk.
Official site: parks.ny.gov/parks/bear-mountain
Tested tip: Stop at Bear Mountain Inn for coffee before hiking. Their outdoor patio overlooks Hessian Lake—perfect for pre-hike photos.
Harriman State Park
10 minutes via Palisades Interstate Parkway
At 47,500 acres, Harriman dwarfs most Northeast parks. The trail network includes 200+ miles, from easy lakeside walks to challenging ridge hikes. Unlike Bear Mountain’s crowds, you’ll find solitude here even on summer weekends.
Popular trailheads:
- Lake Sebago area: Swimming beach, picnic areas, easy trails. Best for families. $10 parking Memorial Day-Labor Day.
- Lake Skannatati: Quieter alternative, smaller crowds, no facilities. Free parking year-round.
- Reeves Meadow: Popular with serious hikers. Connects to Appalachian Trail.
Camping: Multiple campgrounds require advance reservations through Reserve America. Book 2-3 months ahead for summer weekends.
Official site: parks.ny.gov/parks/harriman
Storm King Art Center
25 minutes via NY-32 North
Storm King’s 500-acre sculpture park ranks among the world’s premier outdoor art destinations. The permanent collection includes over 100 works by sculptors like Alexander Calder, Mark di Suvero, and Maya Lin. These aren’t gallery pieces—many sculptures stand 30+ feet tall.
Visiting logistics:
- Season: April through November only. Closed December-March.
- Admission 2025: $25 adults, $22 seniors (65+), $12 students (5-18), free under 5. Tickets often sell out weekends—book online.
- Time commitment: Allow minimum 2 hours. Many visitors stay 3-4 hours. Tram tours available for mobility concerns ($5 additional).
- What to bring: Walking shoes (not sandals), water bottles, sunscreen. Trails include hills and uneven terrain.
Best times: Weekday mornings or late afternoon. Peak fall foliage (mid-October) draws biggest crowds.
Official site: stormking.org
Photography note: Golden hour (last 2 hours before closing) provides stunning light for photos. The south fields with mountain backdrop are particularly dramatic.
Hudson Valley Wine Trail
Brotherhood Winery
20 minutes via NY-17 to Washingtonville
Brotherhood holds the distinction of America’s oldest continuously operating winery, founded in 1839. The underground cellars date to the mid-1800s and maintain constant 55°F temperatures year-round—bring a light jacket even in summer.
Tasting options (2025 pricing):
- Standard tasting: $18, five wines, 45 minutes. No reservation needed weekdays, recommended weekends.
- Cellar tour + tasting: $25, includes historic underground cellars tour (30 min) plus tasting. Tours run hourly.
- Premium reserve tasting: $35, limited-production wines, private room.
What works: The historic atmosphere and underground cellars make this more memorable than typical tasting rooms. Wine quality varies—their sweet wines and fruit wines perform better than their dry reds in my experience.
Official site: brotherhood-winery.com
Warwick Valley Winery & Distillery
15 minutes via NY-17A to Warwick
Warwick Valley built its reputation on hard cider before expanding into spirits. Their Doc’s Draft Hard Cider won multiple awards and put Hudson Valley cider on the map. The farm setting includes apple orchards, barn tasting room, and outdoor seating with orchard views.
Tasting experience:
- Cider flight: $15 for five ciders. Their specialty—go for this over wine.
- Spirits tasting: $18, includes their Black Dirt Bourbon and gin varieties. Small-batch production, interesting if you’re into craft spirits.
- Restaurant on-site: Weekends only, farm-to-table menu, reservations essential. Expect $30-50 per person.
Seasonal bonus: Pick-your-own apples September-October (separate admission, $20-25 per bag). Check their website for orchard opening—weather dependent.
Official site: wvwinery.com
Local insight: Visit midweek if possible. Weekend tastings can get backed up, especially during apple season. The outdoor seating area makes a great lunch stop if you’re combining with Warwick village shopping.
History & Cultural Sites
United States Military Academy at West Point
20 minutes via 9W North
West Point occupies 16,000 acres along the Hudson River’s most dramatic bend. The military academy, founded in 1802, has trained military leaders for over 200 years. The campus combines historic architecture with stunning river views.
Security requirements (mandatory):
- Government-issued photo ID for all adults (driver’s license, passport). No exceptions.
- Vehicle registration and insurance card.
- Expect vehicle inspection at gate—allow extra 15-20 minutes for entry.
- International visitors: passport required.
Visitor Center & Museum (free): Start here. The museum chronicles 200+ years of military history with extensive artifact collections. Budget 1-2 hours minimum. Open daily 10:30am-4:15pm.
Campus tours: Guided tours require advance booking through official tour companies. Self-guided access limited to designated areas. Trophy Point (major memorial site with Hudson views) accessible without tour.
Football games (fall): Home games create major traffic—arrive 2+ hours early. Tickets available through academy athletics website.
Official site: westpoint.edu/visit
Museum Village
15 minutes via NY-17 to Monroe
This 19th-century living history museum recreates Hudson Valley rural life through original and reconstructed buildings. Costumed interpreters demonstrate period crafts and trades in a 16-acre outdoor setting.
What distinguishes this museum: Unlike typical historical displays, Museum Village focuses on everyday life—blacksmithing, weaving, printing, farming. Interactive demonstrations run throughout the day.
Seasonal operation:
- Open: May through October, Wednesday-Sunday
- Closed: November-April
- Special events: Fall harvest festival, Civil War reenactments (check calendar)
Admission: $12-15 adults, $8-10 children (verify current rates)
Time needed: 2-3 hours for full experience
Official site: museumvillage.org
Sugar Loaf Arts & Craft Village
30 minutes via NY-17 and County Route 13
Sugar Loaf concentrates 30+ working artist studios and craft shops in original 17th and 18th-century buildings along one main street. The village maintains its historic character while hosting contemporary artisans.
Shopping distinctions:
- Direct from makers: Pottery, jewelry, textiles, woodwork created on-site. Watch artists work in many studios.
- Price range: Small items $15-50, art pieces $100-500+. Higher than chain retail but reasonable for handcrafted work.
- One-of-a-kind gifts: Everything’s unique. Good for special occasion gifts versus mass-market outlet items.
Dining options: Several cafes and restaurants. The Barnsider Tavern (established 1764) offers casual dining in historic setting.
Best timing: Saturday 11am-4pm sees most studios open. Some close Monday-Tuesday. Spring and fall festivals bring additional vendors and demonstrations.
More details: See our complete Sugar Loaf guide
Family-Friendly Activities
Trailside Museum & Zoo
15 minutes (within Bear Mountain State Park)
Trailside Zoo differs from typical zoos—it houses only native New York wildlife that cannot be released back to the wild due to injury or rehabilitation needs. The compact size (1-2 hours) works perfectly for young children’s attention spans.
Animals you’ll see: Black bears, river otters, bald eagles, owls, bobcats, porcupines, snakes, turtles. All animals have educational signage explaining their stories.
Museum component: Four small museums cover natural history, Native American heritage, and regional geology. Quick walk-throughs, good for rainy day backup.
Practical details:
- Admission: $2 per person (cash only at entrance)
- Hours: Daily 10am-4:30pm, closed Tuesday-Wednesday in winter
- Age sweet spot: Ages 3-10 get most from visit
- Parking: Use Bear Mountain State Park lots (free)
Combine with: Pair with Bear Mountain playground and Hessian Lake for full morning or afternoon.
Official site: trailsidemuseumsandzoo.org
Additional Shopping Options
The Galleria at Crystal Run
20 minutes via NY-17 West to Middletown
Crystal Run functions as Hudson Valley’s main indoor shopping mall. The enclosed format provides weather-proof alternative to Woodbury’s outdoor layout.
Key differences from Woodbury:
- Regular retail pricing: Full-price stores, no outlet discounts
- Different brands: Target, H&M, Forever 21, American Eagle versus Woodbury’s luxury outlets
- Indoor comfort: Climate-controlled, good for extreme weather days
- Dining: Full food court plus sit-down restaurants (Cheesecake Factory, P.F. Chang’s)
When it makes sense: Rain or snow days, need specific items from anchors (Macy’s, Target), prefer mall atmosphere over outlets.
Official site: galleriacrystalrun.com
Warwick Antiques & Vintage District
20 minutes to Warwick village
Warwick’s Main Street concentrates several antique shops, vintage stores, and collectibles dealers within walking distance. The village maintains small-town character with independent shops versus chain stores.
Notable shops:
- Warwick Valley Antique Center: Multi-dealer space, furniture and home goods
- Various Main Street dealers: Specialties range from mid-century modern to farmhouse primitives
- Hours vary: Most open Thursday-Sunday, limited midweek hours
Shopping strategy: Allow 1-2 hours for Main Street walkthrough. Combine with Warwick Valley Winery visit (same area) or lunch at village restaurants.
Parking: Free municipal lots off Main Street. Village walkable once parked.
Planning Your Extended Stay
One-day extension sample itineraries:
Active outdoor: Morning at Bear Mountain (hike to Perkins Tower), lunch at Bear Mountain Inn, afternoon at Storm King Art Center. Total: 6-7 hours.
Wine & culture: Morning at Brotherhood Winery (tour + tasting), lunch in Warwick village, afternoon at Sugar Loaf artisan village. Total: 5-6 hours.
Family day: Morning at Trailside Zoo + Bear Mountain playground, picnic lunch, afternoon at Museum Village. Total: 5-6 hours.
Practical considerations:
- Dining: Options near Woodbury limited. Plan meals in Warwick, Monroe, or at attraction sites.
- Gas stations: Multiple options on NY-17. Fill up before Bear Mountain or West Point drives.
- Cell service: Generally good, but Bear Mountain and Harriman have spotty coverage in valleys.
- Seasonal closures: Storm King and Museum Village close for winter. Check websites before visiting October-April.