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Wedding TransportationSprinter Van ServiceEvent TransportationRoadshow TransportationCity-to-CityPrivate AviationFamily Car ServiceProfessional chauffeur service across all of Orange County, New York -- from the waterfront city of Newburgh to the charming village of Warwick, the halls of West Point to the outlets of Woodbury Common. Vetted chauffeurs who know every Thruway exit, every Route 17 bottleneck, and every back road through the Hudson Highlands, flat-rate airport pricing to Stewart, JFK, LaGuardia, and Newark, and 24/7 availability for 400,000 residents across 30+ communities.
Newburgh · Middletown · West Point · Warwick · Goshen · Woodbury Common · No surge pricing
Orange County is the fastest-growing county in New York State with a population approaching 400,000, stretching from the Bear Mountain Bridge on the east to the Pennsylvania border region on the west. Home to West Point (the United States Military Academy), Woodbury Common Premium Outlets (220+ stores, 13 million annual visitors), Stewart International Airport, and a rapidly expanding logistics corridor along I-87 and I-84, Orange County generates enormous transportation demand -- from military families and international shoppers to corporate executives and weekend visitors from NYC.
Getting to and from Orange County means navigating the I-87 New York State Thruway, a toll road that serves as the primary corridor from NYC. During peak hours, the I-84/I-87 interchange near Newburgh is one of the most congested interchanges in the Hudson Valley. Route 17 (future I-86) through Harriman and Central Valley backs up around Woodbury Common exits on weekends. West Point football Saturdays create severe congestion on Route 9W and Route 293. And apple-picking season transforms the Warwick-Goshen corridor into a slow crawl. Our chauffeurs know every alternative route, every back road, and every real-time workaround.
Whether you need a Stewart Airport transfer, an airport ride to JFK or LaGuardia, an hourly chauffeur for a Woodbury Common shopping day, wedding transportation at Brotherhood Winery, or a reliable pickup after a West Point football game, our vetted chauffeurs and upfront pricing provide a dependable alternative to rideshare surge and Thruway frustration.
From the Hudson River waterfront of Newburgh to the apple orchards of Warwick, our chauffeurs serve every community in Orange County with local routing expertise.
Waterfront city, Stewart Airport, I-84/I-87 interchange, Storm King
Largest city in Orange County, Garnet Health, Route 17/211 corridor
United States Military Academy, Fort Montgomery, Route 9W corridor
Charming villages, apple country, Legoland, harness racing, county seat
Woodbury Common Premium Outlets, I-87 Exit 16, Museum Village
Southern Orange County gateway, state parks, rail access
Our most-requested Orange County pickup and drop-off locations, with specific logistics our chauffeurs handle regularly.
1180 1st St, New Windsor
Orange County's own commercial airport serving Breeze Airways and Allegiant Air. Smaller terminal means quick curbside pickups. Your chauffeur monitors flight status and waits at the terminal exit. 10 minutes from Newburgh, 20 minutes from Middletown.
498 Red Apple Ct, Central Valley
220+ stores across 800,000 sq ft. Weekend parking lots hold 8,200+ vehicles and fill quickly. Your chauffeur drops you at the entrance, parks nearby, and returns on demand -- no circling for spaces, no hauling bags across massive lots.
U.S. Military Academy, West Point
Strict security protocols require advance coordination for vehicle access. Graduation ceremonies, football games at Michie Stadium (38,000 capacity), and cadet events all require pre-positioned pickup logistics. We coordinate with USMA visitor procedures.
1 Museum Rd, New Windsor
500-acre outdoor sculpture park open April through November. Located off Route 32 near Mountainville. Curbside drop-off at the visitor center entrance. Fall foliage weekends draw peak crowds -- your chauffeur uses Route 9W alternatives.
100 Brotherhood Plaza Dr, Washingtonville
The oldest continuously operating winery in the United States (established 1839). Popular wedding and event venue. Your chauffeur navigates the rural Route 94/208 corridor and provides a safe ride home after tastings.
Stewart Airport is right in Orange County for domestic flights. For broader airline selection, JFK, LaGuardia, and Newark are all reachable via I-87. Your chauffeur selects the optimal route based on real-time Thruway conditions.
Local airport — 10-30 min
1.5-2+ hours from Orange County
1.25-1.75 hours from Orange County
1.25-1.75 hours from Orange County
Every airport transfer includes: Real-time flight monitoring, automatic delay adjustments, meet-and-greet option at baggage claim, luggage assistance, and flat-rate pricing locked at booking -- no surge regardless of weather, Thruway conditions, or demand. Learn more about airport services.
From world-class outdoor sculpture to the oldest winery in America, West Point traditions to outlet shopping -- Orange County offers extraordinary destinations that all require local navigation expertise.
The United States Military Academy at West Point hosts graduation ceremonies, football games at Michie Stadium, and events that draw tens of thousands. Route 9W and Route 293 create severe bottlenecks. Our chauffeurs coordinate with USMA visitor protocols and pre-position vehicles for seamless pickups.
Woodbury Common Premium Outlets draws 13 million visitors annually to 220+ stores. Weekend traffic near I-87 Exit 16 and Route 17 is notorious. Our hourly chauffeur service eliminates parking hassles, bag hauling, and navigation stress -- especially popular with international tourist groups.
Storm King Art Center in New Windsor is one of the world's premier outdoor sculpture parks, spanning 500 acres with works by Calder, Serra, and Goldsworthy. Open April through November, with peak attendance during fall foliage weekends. Combine with a Brotherhood Winery visit for a full Hudson Valley day trip.
Orange County's wedding venues include Brotherhood Winery (est. 1839), Falkirk Estate in Central Valley, Mansion Ridge in Monroe, and Anthony's Pier 9 in New Windsor. Rural roads and limited signage make professional transportation essential for guests arriving from NYC.
Orange County's I-87/I-84 corridor hosts Amazon fulfillment centers, UPS facilities, and a growing tech sector in Newburgh. Garnet Health Medical Center in Middletown is a major employer. Our corporate car service provides consolidated invoicing and dedicated chauffeurs for executive travel.
Legoland New York Resort in Goshen (opened 2021) is Orange County's newest major attraction, drawing families from across the tristate area. Route 17A traffic on weekends and holidays can be significant. Child seats are available for $25 each, and your chauffeur handles the navigation so you can focus on the kids.
Four steps from booking to arrival. The entire process takes under two minutes online.
Enter your Orange County pickup address, destination, date, and time. Select your vehicle from our fleet -- sedan, SUV, or sprinter. Get an instant flat-rate quote with no hidden fees.
Include flight numbers for Stewart or NYC airport transfers, event end times for West Point games, or specific pickup instructions for Woodbury Common. Note any child seat needs for Legoland trips.
Your vetted chauffeur arrives at your exact Orange County location -- home driveway, Stewart Airport terminal, West Point gate, or Woodbury Common entrance. You receive a text with vehicle details and chauffeur contact.
Your chauffeur navigates Orange County roads using real-time routing -- I-87 Thruway alternatives, Route 17 bypass options, and Route 9W workarounds. For airport transfers, luggage assistance and terminal drop-off are included.
We monitor your flight in real-time. For domestic arrivals at Stewart, JFK, LaGuardia, or Newark, your chauffeur waits up to 45 minutes after landing at no charge. For international arrivals, up to 60 minutes. If your flight is delayed, we adjust automatically.
Provide your flight number at booking and we handle the rest. Our system tracks arrivals from Stewart, JFK, LaGuardia, and Newark and dispatches your chauffeur based on actual landing time -- not the scheduled time.
Free cancellation up to 24 hours before your scheduled pickup. Cancellations within 24 hours may incur a partial charge. No-shows are charged the full fare. All cancellation policies are confirmed at booking.
Rear-facing, forward-facing, and booster seats available for $25 each. Ideal for Legoland and family trips. Select during booking and specify ages/weights. Seats arrive pre-installed and safety-checked by your chauffeur.
Background-checked, professionally trained, and deeply familiar with Orange County highways, rural roads, and the I-87/I-84 interchange system.
Our chauffeurs know every I-87 exit, every Route 17 bottleneck, and every Palisades Parkway alternative -- saving you 20-40 minutes on congested days.
Real-time monitoring for Stewart, JFK, LGA, and EWR flights. Automatic timing adjustments for delays -- your chauffeur is there when you land, not when the schedule says.
Flat-rate quotes locked at booking. No surge during Thruway congestion, West Point football Saturdays, Woodbury Common weekends, or holiday apple-picking season.
From Stewart Airport transfers to West Point graduation logistics, Woodbury Common shopping trips to Brotherhood Winery weddings -- vetted chauffeurs, flat-rate pricing, and zero surge across all of Orange County. Explore our fleet or view all Hudson Valley services.
Last updated: February 2026
True North VIP is a New York City-based premium chauffeur and black car service. The company provides airport transfers to JFK, LaGuardia, Newark, Teterboro, and Westchester County airports, along with hourly charters, corporate ground transportation, wedding and event service, and city-to-city travel. Service covers all five NYC boroughs, Northern New Jersey, Connecticut, Westchester County, Long Island, and the Hamptons, with vetted professional chauffeurs and a fleet of executive sedans, luxury sedans, SUVs, and Sprinter vans available 24/7.
To book a ride, visit truenorthvip.com/book or call +1‑347‑321‑9929.
