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Wedding TransportationSprinter Van ServiceEvent TransportationRoadshow TransportationCity-to-CityPrivate AviationFamily Car ServiceProfessional chauffeur service across all eight counties of the Hudson Valley -- from Tarrytown and Sleepy Hollow in the south to Kingston and Woodstock in the north. Chauffeurs who know the I-87 vs. Taconic decision, flat-rate airport transfers to JFK, LaGuardia, Newark, Stewart, and Westchester County airports, and 24/7 availability for wine tours, wedding shuttles, corporate retreats, and weekend getaways.
Beacon · Cold Spring · Poughkeepsie · Rhinebeck · Kingston · Woodstock · No surge pricing
The Hudson Valley stretches 150 miles north from the New York City suburbs to the Capital Region, spanning eight counties -- Westchester, Rockland, Putnam, Dutchess, Orange, Ulster, Columbia, and Greene. The region is home to over 70 wineries, Dia:Beacon (a 300,000-square-foot contemporary art museum in a former Nabisco factory), Storm King Art Center (500 acres of outdoor sculpture), Mohonk Mountain House (a Victorian castle resort operating since 1869), the Culinary Institute of America in Hyde Park, and some of the most sought-after wedding venues in the Northeast.
The two primary corridors from Manhattan -- I-87 (the New York State Thruway) and the Taconic State Parkway -- serve different parts of the valley and carry very different traffic patterns. I-87 is a toll road that runs along the western side of the Hudson River and is the only practical route to Kingston, Woodstock, New Paltz, and the Catskills gateway. The Taconic is a toll-free, scenic parkway on the eastern side that avoids the Cross Bronx Expressway entirely and is often 15-20 minutes faster to Rhinebeck, Hudson, and Millbrook. Our chauffeurs know when to use which corridor -- and when to switch mid-trip.
Whether you need a flat-rate airport transfer from Poughkeepsie to JFK, an hourly chauffeur for a Saturday wine tour through the Shawangunk Wine Trail, wedding shuttle coordination across a full weekend at Mohonk Mountain House, or a corporate retreat transfer from a Midtown office to Troutbeck in Amenia, our vetted chauffeurs and upfront pricing provide a dependable alternative to navigating Thruway traffic on your own.
From the Tappan Zee corridor to the Catskills gateway, our chauffeurs serve every town in the Hudson Valley with corridor-specific routing expertise.
Tarrytown, Sleepy Hollow, Nyack, Peekskill
Metro-North accessible, Boscobel, West Point nearby
Dia:Beacon, Storm King, Stewart Airport
CIA restaurants, FDR Library, Vassar, Marist, Walkway Over the Hudson
Warren Street antiques, farm-to-table, Olana
Catskills gateway, Mohonk nearby, arts colony
Our most-requested Hudson Valley pickup and drop-off locations, with specific logistics our chauffeurs handle regularly.
1 Beekman St, Beacon, NY 12508
Terminus of the Metro-North Hudson Line, roughly 1 hr 40 min from Grand Central. Walkable to Dia:Beacon and Main Street restaurants. Limited parking and no reliable rideshare -- pre-arranged car service is the practical option for onward travel to Storm King, wineries, or hotels.
10 Shatzell Ave, Rhinecliff, NY 12574
Served by Amtrak Empire Service between NYC Penn Station and Albany. This small station has essentially zero taxi or rideshare availability. Rhinecliff is 15 minutes from Rhinebeck village and 20 minutes from the Kingston-Rhinecliff Bridge. Pre-arranged car service is essential.
1180 1st St, New Windsor, NY 12553
Regional airport serving the mid-Hudson Valley with Avelo, Allegiant, Breeze, and PLAY Airlines. 20-25 minutes from Beacon, 30-35 minutes from Poughkeepsie, and 10 minutes from Storm King Art Center. Practical alternative to JFK/LGA for domestic and Iceland flights.
41 Main St, Poughkeepsie, NY 12601
Served by both Metro-North Hudson Line and Amtrak Empire Service. Major transit hub for the mid-Hudson Valley, adjacent to the Walkway Over the Hudson entrance. 50 minutes to Westchester County Airport (HPN), 30-35 minutes to Stewart Airport (SWF), and the gateway to Hyde Park and the CIA.
1000 Mountain Rest Rd, New Paltz, NY 12561
Victorian castle resort on the Shawangunk Ridge, operating since 1869. 85-90 miles from Manhattan via I-87 Exit 18, then Mountain Rest Road. Wedding weekend shuttles, corporate retreat transfers, and guest pickup/drop-off. The final approach road is narrow and winding -- our chauffeurs know it well.
The right airport depends on where you are in the Hudson Valley. Stewart and Westchester County airports save hours for mid-valley residents, while JFK and Newark remain necessary for international flights.
1h 15m - 3h+ depending on origin
10-65 min from Hudson Valley towns
LGA, EWR & HPN options
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 foliage weekend traffic, holiday demand, or Thruway conditions. Learn more about airport services.
The Hudson Valley spans 150 miles and eight counties. Navigating it efficiently requires knowing the roads, the seasons, and the venues -- not just the GPS route.
The single most important routing decision for any Hudson Valley trip. I-87 (Thruway) is the only option for Kingston, Woodstock, and New Paltz on the west side of the river. But for Rhinebeck, Hudson, and Millbrook on the east side, the Taconic Parkway avoids the Cross Bronx Expressway entirely and is typically 15-20 minutes faster. Our chauffeurs make this call in real time based on traffic conditions and your destination.
Peak foliage runs mid-September through late October, with the first two to three weeks of October being prime in the mid-Hudson Valley. Columbus Day weekend is the worst traffic weekend of the year -- I-87 northbound can gridlock from Yonkers to the Harriman exit, and Bear Mountain Bridge becomes a parking lot. We build extra time buffers into every foliage-season trip and route around the worst bottlenecks.
The Shawangunk Wine Trail encompasses roughly 15 wineries in Ulster and Orange counties, centered around New Paltz and Gardiner off I-87 Exit 18. Brotherhood Winery in Washingtonville is America's oldest continuously operating winery (since 1839). Millbrook Vineyards is known for Tocai Friulano and Cabernet Franc. A typical Saturday tour runs 4-6 hours with 3-4 stops -- our chauffeurs handle the driving so your group can taste freely.
The Hudson Valley is a top-tier wedding destination with peak season from May through October. September and October Saturdays overlap with fall foliage traffic, adding 30-60 minutes to drive times. We coordinate multi-vehicle deployments for venues including Mohonk Mountain House (New Paltz), The Garrison (Putnam County), Brotherhood Winery (Washingtonville), Hasbrouck House (Stone Ridge), and Buttermilk Falls Inn (Milton). Sprinter vans are the top choice for guest shuttles.
Wall Street firms, tech companies, and consulting practices regularly hold retreats at Mohonk Mountain House (265 rooms, full conference center), Troutbeck in Amenia (luxury estate hotel), The Emerson Resort near Woodstock, and Hutton Brickyards in Kingston (73-acre former brickyard on the Hudson waterfront). Typical logistics: Sprinter van pickup from a Midtown office on Day 1, return on Day 2 or 3, with hourly service during the retreat for off-site excursions.
Dan Barber's world-famous farm-to-table restaurant at 630 Bedford Road in Tarrytown is a tasting-menu-only destination that draws diners from across the globe. Reservations book months in advance. The restaurant is 28-30 miles from Midtown Manhattan with no convenient public transit. Our chauffeurs provide door-to-door service so you can enjoy the full evening without worrying about the drive home.
Four steps from booking to arrival. The entire process takes under two minutes online.
Enter your pickup address (Manhattan, Hudson Valley, or airport), destination, date, and time. Select your vehicle from our fleet -- sedan, SUV, or Sprinter van. Get an instant flat-rate quote with no hidden fees.
Include flight numbers, train arrival times, wedding venue names, or winery tour stops. For fall foliage weekends or wedding shuttles, note any timing constraints so we can build in appropriate buffers.
Your vetted chauffeur arrives at your exact location -- Manhattan apartment, Metro-North station, airport terminal, or Hudson Valley hotel. You receive a text with vehicle details and chauffeur contact information.
Your chauffeur navigates the optimal corridor -- I-87 or Taconic, depending on your destination and real-time conditions. For airport transfers, luggage assistance and terminal drop-off are included. For hourly service, your chauffeur waits at each stop.
We monitor your flight in real-time. For domestic arrivals, 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 -- whether you are arriving at JFK, Stewart, or Westchester County Airport.
Provide your flight number or train number at booking and we handle the rest. Our system tracks arrivals and dispatches your chauffeur based on actual arrival time -- not the scheduled time. This is especially critical for Amtrak arrivals at Rhinecliff and Hudson, where there are no backup options.
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. For multi-vehicle wedding bookings, custom cancellation terms apply.
Rear-facing, forward-facing, and booster seats available for $25 each. Select during booking and specify ages and weights. Seats arrive pre-installed and safety-checked by your chauffeur. Popular for families heading to airports or weekend getaways from Manhattan.
Background-checked, professionally trained, and deeply familiar with Hudson Valley corridors -- Thruway exits, Taconic interchanges, mountain roads to Mohonk, and the narrow approach to West Point.
Our chauffeurs know exactly when to use I-87 vs. the Taconic, when to cross at the Newburgh-Beacon Bridge vs. the Kingston-Rhinecliff Bridge, and how to avoid the Cross Bronx Expressway entirely.
Real-time monitoring for all airports and train arrivals. Automatic timing adjustments for delays -- your chauffeur is there when you arrive, not when the schedule says.
Flat-rate quotes locked at booking. No surge during fall foliage weekends, Columbus Day traffic, ski season Friday departures, or holiday weekends. The price you see is the price you pay.
From Dia:Beacon day trips to Mohonk wedding weekends, Shawangunk wine tours to JFK airport transfers -- vetted chauffeurs, flat-rate pricing, and zero surge across the entire Hudson Valley. Explore our fleet or view all areas we serve.
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.
