Escape for a romantic weekend from Ontario to Upstate New York’s cozy retreats, scenic wineries, and charming small towns. Whether you’re looking for a quiet lakeside getaway, a wine-tasting adventure, or just a scenic drive together, this one-way road trip is perfect for couples seeking intimacy and adventure. And the best part? You can take this route in either direction, making it a flexible option for planning your next romantic escape.
Planning your trip is easier than ever with US Canada Auto Transport. Ship your vehicle one-way and enjoy the freedom of exploring without the worry of returning your car.
Why This Route Works for Couples
Starting in Ontario, you can cross into New York via a smooth border crossing at Niagara Falls or Buffalo. Early in your journey, take a detour to Niagara-on-the-Lake, famous for its quaint streets and award-winning wineries. For scenic drives and romantic photo opportunities, Upstate New York offers endless options, from the Finger Lakes region to charming villages like Skaneateles and Cooperstown.
If you’re curious about traveling within the U.S., check out our New York state guide for tips on shipping your car to New York from Ontario and other travel advice.
Day-by-Day Romantic Highlights
Day 1: Ontario → Niagara-on-the-Lake
Drive time: ~2 hours
Start your escape by heading to Niagara-on-the-Lake. Stroll along its historic streets, enjoy boutique shopping, and indulge in wine tasting at Peller Estates Winery. For dinner, savor a farm-to-table meal at Treadwell Cuisine. Stay overnight at the historic Prince of Wales Hotel, a perfect mid-range romantic retreat.
Day 2: Niagara-on-the-Lake → Finger Lakes
Drive time: ~4 hours
Cross into the U.S. via Buffalo, NY, and explore the Finger Lakes region. Make a scenic stop at Letchworth State Park, known as the “Grand Canyon of the East.” Taste local wines at Dr. Konstantin Frank Winery and enjoy an intimate dinner at FLX Table. Overnight at Belhurst Castle, a romantic mid-range hotel on Seneca Lake.
Day 3: Finger Lakes → Ithaca
Drive time: ~1 hour
Drive along Seneca Lake’s scenic Route 89 and visit Watkins Glen State Park for stunning waterfalls. Lunch at Moosewood Restaurant, then a relaxing afternoon wine tasting at Sheldrake Point Winery. Dinner at Just a Taste Wine & Tapas Bar and overnight at Statler Hotel at Cornell University.
Day 4: Ithaca → Skaneateles
Drive time: ~2 hours
Explore the Finger Lakes Wine Country Route with a stop at Taughannock Falls State Park. Enjoy a lakeside lunch at Bluewater Grill, wine tasting at Rosalie Vineyards, and dinner at Penelope’s Restaurant. Stay overnight at the charming Sherwood Inn.
Day 5: Skaneateles → Cooperstown
Drive time: ~2.5 hours
Discover Cooperstown’s quaint charm and the Baseball Hall of Fame. Scenic stops at Glimmerglass State Park enhance the romance of your journey. Lunch at Otesaga Hotel Tap Room and dinner at Nicoletta’s Italian Restaurant. Overnight at The Otesaga Resort Hotel.
Day 6: Cooperstown → Hudson Valley
Drive time: ~3.5 hours
Drive through the Catskills Mountains to Hudson Valley. Visit Storm King Art Center for a romantic sculpture walk. Lunch at Blue Hill at Stone Barns, dinner at Café Fiorello, and overnight at Mohonk Mountain House, a cozy mid-range retreat.
Day 7: Hudson Valley → Ontario
Drive time: ~6–7 hours
Begin your journey home with a leisurely breakfast, optional detour at Walkway Over the Hudson, and enjoy a casual lunch en route. This last stretch allows you to reflect on your scenic and romantic escape.
Scenic Stops and Tips for Couples
- Border Crossing: Keep passports handy and check customs regulations before entering the U.S.
- Wine Tastings: Reservations are recommended for the Finger Lakes and Niagara-on-the-Lake wineries.
- Packing: Bring cozy layers for lake walks and cooler evenings.
- Flexibility: This route can also be taken northbound from New York to Ontario, giving you freedom in planning.
Use our Road Trip Planner to customize your route and map out must-see stops for your romantic journey.
For additional inspiration, check out our New York to Ontario (or Vice Versa): The Great Lakes Getaway blog for more ideas.
Final Thoughts
Whether you’re heading south from Ontario to Upstate New York or taking the reverse route, this romantic weekend escape is packed with charming towns, scenic drives, and unforgettable wine tastings. Plan your route with our Road Trip Planner and let US Canada Auto Transport handle your one-way car shipping, so you can focus on creating memories together.
Google Maps Itinerary
View the full Ontario to Upstate New York road trip itinerary on Google Maps
