History, Art & Adventure in Orange County, NY

Discover a fresh side of the Hudson Valley in Orange County where groups can experience iconic American history and world-class shopping

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Is This Itinerary Right For Your Group?

Ideal Demographic: Seniors, active adults
Size Bottleneck: Depends on venues but generally group-friendly.
Mobility: Mixed
Peak Window: Summer, Fall Foliage
Booking Lead Time: Varies by venue

Discover a fresh side of the Hudson Valley in Orange County where groups can experience iconic American history and world-class shopping

Planner's Hotline: Your Local Advocate

Rachel Carr

Tourism Coordinator
Orange County Tourism & Film
Rcarr@orangecountygov.com
www.pickocny.com

Click Here to Connect with Orange County

Day 1: Visit an iconic art museum

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Day 1 Alternatives

Founded in 1839, Brotherhood Winery is America’s oldest continuously operating winery and a proven favorite for group tours in the Hudson Valley. Groups can explore historic wine cellars, enjoy guided tastings of award-winning wines, and experience a destination with deep winemaking heritage. With experience hosting hundreds of groups each season and flexible programs for senior, student, FIT, and corporate groups, Brotherhood offers tour operators a reliable, travel-trade-friendly experience that adds history, culture, and wine to any Hudson Valley itinerary.

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Midday:

Arrive in Orange County and begin your tour with a visit to Woodbury Common Premium Outlets. A premier shopping destination with 250+ designer and brand-name stores, Woodbury Common offers groups an easy-to-add retail experience in an outdoor village-style setting. Motorcoach groups receive dedicated parking and welcome services, with tour operator and group programs available to help operators coordinate visits and provide passenger incentives.

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Afternoon:

For lunch, pay a visit to Cosimo’s, a casual Italian trattoria. Conveniently located near Woodbury Common Premium Outlets, Cosimo’s Woodbury is an ideal dining stop for groups combining shopping and sightseeing in the Hudson Valley. Cosimo’s features farm-to-table Italian comfort food, featuring wood-fired brick oven pizzas. Storm King Art Center is an iconic 500-acre outdoor museum in the heart of the Hudson Valley and is one of the world’s leading sculpture parks, combining large-scale sculpture, art, and landscape across expansive meadows, wooded areas, and rolling hills. Ideal for group tours and cultural MICE programs, Storm King offers guided adult group tours led by docents and museum educators, including Art & Landscape and Museum Hill History and Highlights tours, as well as tram tours, bicycle rentals, and an open-air café. Moderate walking on uneven terrain is required, and seasonal hours apply. Bus parking is available.

Day 2 LEGOLAND awaits you

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Evening

Limoncello at the Orange Inn offers groups a seamless dining experience with two completely private dining rooms and all-inclusive menu options. Its flexible spaces and dedicated service make it an ideal choice for group lunches, dinners, and special events.

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Morning:

LEGOLAND New York Resort is a 150-acre theme park featuring 50+ interactive rides, live shows and attractions across seven themed lands, LEGOLAND New York Resort offers a full-day experience geared toward families and youth groups. With hands-on attractions, LEGO-themed rides, live entertainment and educational programming, it is particularly well suited to school, youth and family group itineraries. The resort also features an on-site LEGOLAND Hotel, providing a convenient overnight option that allows groups to extend their visit into a multi-day experience.
Another option today is to visit Christopher Jacobs Pennings Vineyards. Located just 1–1.5 hours from NYC in Northern Orange County, Christopher Jacobs Winery offers groups an authentic Hudson Valley farm and vineyard experience. Groups can enjoy estate-grown Hudson River Region AVA wines, meet the owners and winemakers, and take in scenic vineyard views. The winery welcomes motorcoaches of 30–60 passengers and offers guided wine tastings and vineyard tours, a Wine, Taste & Tour package for groups of 15–30, and a Wine & Horse Trail Ride package for groups of 10+. With spacious indoor and outdoor seating, seasonal food trucks and live music, and family-friendly programming, it’s an easy addition to a Hudson Valley group itinerary.

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Day 2 Alternatives

Tin Barn Brewing offers groups a lively Hudson Valley experience combining craft beer, artisan food, live music, and events all in one stop. Located in Chester, just off NY-17 and close to Sugar Loaf, LEGOLAND New York, and Woodbury Common, the family-owned farm brewery can accommodate 700+ guests and is ideal for group tours, FITs, and MICE. Guests can enjoy hazy IPAs, creative sours, barrel-aged stouts, stone-fired pizza, burgers, and seasonal programming, with expanded outdoor capacity during the summer and fall.

Day 3 West Point will awe you

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Morning

Explore the history, traditions and leadership legacy of the United States Military Academy at West Point through year-round guided tours. West Point Tours accommodates single or multiple motorcoach groups, with options ranging from the 1-hour-15-minute West Point Story to specialized tours focused on the American Revolution, West Point history and traditions, or leadership—ideal for student, senior, corporate, MICE and military-related groups. Tours include off-bus stops at highlights such as Trophy Point, the Parade Ground and Cadet Chapel, with customizable itineraries and step-on guides available. Free motorcoach parking and tour pickup/drop-off are available at the West Point Visitors Center. Because West Point is an active military installation, all guests must present valid U.S. identification or an international passport, and private groups must submit a passenger manifest 10–14 days in advance for security clearance.

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Afternoon:

MacArthur’s Riverview Restaurant offers groups a memorable dining experience in the historic Thayer Hotel at West Point. With American Gothic windows, old- world charm, and scenic Hudson River views, it provides a distinctive setting for group breakfasts, lunches, and dinners, as well as its award-winning Sunday Champagne Brunch.
After lunch, pay a visit to Angry Orchard Cider House, which offers groups a unique Hudson Valley experience in its scenic orchard setting, with motorcoach drop-off and dedicated bus parking. Private group options include behind-the-scenes cider production tours, guided tastings of limited-production ciders, and the signature Treehouse Experience, which combines an orchard tour with a tasting. Custom experiences and catering are also available, making Angry Orchard an easy and memorable addition to group itineraries.

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Day 3 Alternatives

One of the Hudson Valley’s newest wineries with its own vineyard, Christopher Jacobs Winery at Pennings Vineyards features an outdoor tasting room with vineyard views and a picnic area. U-pick grapes are available from the end of August through September, and the winery is open from the end of May through October, Saturdays and Sundays, 12-5 p.m.

Planning your next group tour? Get fresh itinerary ideas and destination inspiration in InSite from Leisure Group Travel.

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How much time should planners allow for Storm King Art Center, and what are the best options for groups with different mobility levels?

Planners should allow at least a half day for Storm King, particularly if they want the group to experience more than a quick sampling of the sculpture grounds. The 500-acre property is expansive, and the combination of outdoor sculpture, landscape and walking trails means the amount of time needed depends on how much of the grounds the group wants to cover.
For groups with mixed mobility, the tram is a particularly useful option because it allows visitors to see more of the property without walking the entire grounds. Guided tours can also be tailored to a group’s interests. Visitors who are comfortable walking can explore the meadows and sculpture installations at their own pace, although planners should warn travelers that some paths and terrain are uneven.

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How can planners customize a West Point visit for different types of groups, and what advance information or documentation is required?

West Point offers considerable flexibility for group planners. The standard West Point Story tour runs about 1 hour and 15 minutes, while specialized tours can focus on subjects such as the American Revolution, West Point history and traditions, or leadership. Groups can also work with West Point Tours to develop customized itineraries, and step-on guides are available. That makes the attraction adaptable for senior groups, history buffs, students, military-related groups and corporate/MICE travelers.