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Wedding TransportationSprinter Van ServiceEvent TransportationRoadshow TransportationCity-to-CityPrivate AviationFamily Car ServiceProfessional chauffeur service throughout Rye and Rye Brook in Westchester County. From I-95 corridor airport transfers to Merritt Parkway-compliant Connecticut crossings, country club event logistics to Rye Brook corporate commutes -- vetted chauffeurs who know every exit, flat-rate pricing, and 24/7 availability.
HPN 13 min · LGA 30 min · JFK 40 min · EWR 50 min · No surge pricing
Rye and Rye Brook occupy a privileged stretch of Westchester County's Gold Coast -- affluent commuter suburbs on Long Island Sound where the median household income exceeds $237,000 and expectations for service quality match. True North VIP provides professional chauffeur service calibrated to this community, from early-morning airport departures on I-95 to late-evening returns from Manhattan dinners.
The I-95 corridor (New England Thruway) runs directly through Rye with three key exits: Exit 19 at Playland, Exit 20 at Boston Post Road, and Exit 22 at the Connecticut border. The Hutchinson River Parkway connects south to Cross County Parkway and the Bronx. Our chauffeurs know these arteries and their congestion patterns -- Playland Parkway gridlock on summer evenings, I-95 bottlenecks at the Cross Westchester merge, and the afternoon backup at the Greenwich toll approach. Every airport transfer is routed in real time based on current conditions.
Whether you need a point-to-point transfer from Rye to JFK, an hourly chauffeur for a day of meetings along the I-287 corridor, corporate account service for your Rye Brook office, or wedding transportation at one of the legendary country clubs, our vetted chauffeurs and flat-rate pricing provide a seamless alternative to rideshare uncertainty. As part of our broader Westchester car service, every Rye ride benefits from deep local knowledge.
From the downtown village to the corporate corridor, waterfront estates to the Connecticut border -- our chauffeurs know the pickup logistics for every corner of Rye and Rye Brook.
Boston Post Road corridor, Purchase Street shops
American Yacht Club, Rye Golf Club, Whitby Castle
Playland amusement park, 1,200-ft beach, seasonal events
Hilton Westchester, 800 Westchester Ave, I-287 corridor
Westchester CC, Coveleigh Club, Apawamis Club
I-95 Exit 22, gateway to Greenwich, Merritt Parkway access
Our most-requested pickup and drop-off locations across Rye and Rye Brook, with the specific logistics our chauffeurs handle regularly.
New Haven Line, Purchase Street
40-minute express to Grand Central. Commuter parking lot pickup and drop-off. Ideal staging point for early-morning airport transfers or late-night Manhattan returns.
699 Westchester Ave, Rye Brook
445-room hotel and conference center. Corporate meeting transportation, airport transfers for visiting executives, and event logistics at the main entrance porte-cochere.
Playland Pkwy off I-95 Exit 19
Seasonal amusement park on Long Island Sound. Summer congestion avoidance via pre-staged vehicle in the main lot. Text with exact pin sent before your pickup time.
99 Biltmore Ave, Rye
1,600+ member club hosting weddings, galas, and corporate events. Multi-vehicle staging at the main entrance with coordination for event timelines and guest shuttles.
Boston Post Rd waterfront
1,200-foot beach on Long Island Sound. Seasonal events and summer weekend pickups. Parking fills early -- curbside staging on Dearborn Avenue for reliable pickup.
Rye's position on I-95 gives you access to four airports. HPN is the closest and most convenient -- the NYC airports are straightforward via the New England Thruway south.
Closest — 10 mi, 13-16 min
23 mi, 30-40 min off-peak
31 mi, 40-50 min off-peak
39 mi, 50-60 min off-peak
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, traffic, or demand. Learn more about airport services.
Rye and Rye Brook demand a chauffeur who understands private club protocols, corporate corridor logistics, Metro-North timing, Merritt Parkway rules, and seasonal Playland congestion.
Westchester Country Club, Coveleigh Club, Apawamis Club, and Whitby Castle host weddings, galas, and member events year-round. We coordinate multi-vehicle staging, bridal party transfers, and guest pickup at club-specific entrances.
The Rye Brook office corridor along Westchester Avenue -- Hilton Westchester, 800 Westchester Ave complex, and I-287 access -- generates daily executive transportation. Airport transfers for visiting clients and recurring commuter service with monthly invoicing.
The Rye station on the New Haven Line runs 40 to 45-minute express trains to Grand Central -- but our door-to-door service is faster for airport connections, late-night returns, and any trip involving luggage or multiple Manhattan stops.
The Merritt bans vehicles over 8 ft tall, 24 ft long, or 7,500 lbs -- plus commercial plates. Our sedans and standard SUVs comply fully, giving your chauffeur the faster, scenic Merritt route into Connecticut instead of congested I-95.
Playland Parkway -- the 1.5-mile spur from I-95 Exit 19 -- becomes a bottleneck on summer weekends. We pre-stage vehicles in the park lot and time departures to avoid the post-fireworks and post-beach exit crush that gridlocks the parkway.
Rye and Greenwich share the I-95 Exit 22 border crossing. We handle daily cross-border trips -- Rye to Greenwich Avenue dining, back-country estates, Old Greenwich waterfront, and Stamford corporate offices. No surcharge for Connecticut destinations.
Four steps from booking to arrival. The entire process takes under two minutes online.
Enter your Rye or Rye Brook 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, club event times, hotel names, or specific pickup instructions. For Playland or country club events, note your expected exit time so we can pre-stage your vehicle.
Your vetted chauffeur arrives at your exact location -- home driveway, Metro-North station, Hilton entrance, or club valet. You receive a text with vehicle details and chauffeur contact.
Your chauffeur navigates I-95, the Hutch, or the Merritt using real-time routing. For airport transfers, luggage handling and terminal drop-off are included. For events, your chauffeur stages and waits.
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 land at HPN, LGA, JFK, or EWR.
Provide your flight number at booking and we handle the rest. Our system tracks arrivals from all four airports and dispatches your chauffeur based on actual landing time -- not the scheduled time. This is especially valuable for Rye pickups timed to late-evening arrivals.
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. Select during booking and specify ages and weights. Seats arrive pre-installed and safety-checked by your chauffeur -- popular for families heading to the airports from Rye.
Background-checked, professionally trained, and deeply familiar with the I-95 corridor, Westchester back roads, and country club protocols throughout Rye and Rye Brook.
Our sedans and standard SUVs meet every Merritt Parkway restriction -- height, length, weight, and plate type. Your chauffeur can take the scenic route into Connecticut without detour.
Real-time monitoring for HPN, 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 rush hour, summer Playland congestion, or country club galas. The price you see is the price you pay.
From I-95 airport transfers to Merritt Parkway Connecticut crossings, country club galas to Rye Brook corporate commutes -- vetted chauffeurs, flat-rate pricing, and zero surge across Rye and Rye Brook. Explore our fleet or view all Westchester 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.
