Romantic Getaways in Upstate NY: 3 Fairytale Regions You’ll Love

Planning a trip for two to Upstate New York? Then this is the blog for you! There’s a reason couples return to the mountains, forests, and lakes of New York State again and again. Upstate New York feels like an antidote to the speed and stress of modern life. Here, quiet mornings, days spent exploring nature, and quiet evenings by the fireside set the stage for conversation, adventure, and romance. Whether you’re drawn to the majesty of the Catskill Mountains, the artsy charm of the Hudson Valley, or the atmospheric beauty of the Finger Lakes, Upstate New York offers something for couples of kinds. Learn more about our picks for the most romantic getaways in Upstate NY, as well as a unique boutique that immerses you in nature without skimping on comfort. Let’s get started!

Romantic Getaways in Upstate NY: The Catskills (Endless Activities for Outdoorsy Couples)

The Catskills might be the most romantic region in Upstate New York, and it’s no wonder. The mountains are gentle rather than imposing, the towns artistic instead of crowded, and nearly everything here encourages slowing down together.

Romantic Things to Do Outdoors

• Waterfall Hikes – Upstate New York is home to tons of short, scenic trails that lead to dramatic waterfalls, perfect for a picnic and a couple cute selfies. Even casual hikers can reach spectacular views in less than an hour.
• Fly Fishing or River Walks – The Delaware River and its offshoots are peaceful and surprisingly romantic, even if you never cast a line.
• Forest Bathing – The Catskills are dense with old, almost cathedral-like hardwood forests, offering a meditative setting ideal for agenda-free wandering.
• Stargazing – Many areas in Upstate NY have low light pollution, making them ideal for an intimate evening of stargazing.

Upstate New York Getaways for Two: Hudson Valley (Art Walks, River Walks, and Hiking in Esopus Bend Nature Preserve)

The Hudson Valley in Upstate NY offers a slightly different take on the romantic getaway. Historic, artistic, and visually striking, the region offers a unique blend of natural beauty and rustic-village charm.

Romantic outdoor highlights include:

• Hudson River River Walks –Elevated rail trails and bridge walks overlooking the Hudson River offer the perfect opportunity for a romantic stroll.
• Esopus Bend Nature Preserve –Cliffside hikes and scenic lookout points ideal for watching the sunset make this a must for couples seeking adventure.
• Art Walks –Outdoor art installations and sculpture gardens abound in the Hudson Valley.
• Scenic Drives –Especially lovely during fall foliage, scenic drives are a must for your romantic getaway to the Hudson Valley in New York State.

The Best Romantic Weekend Getaways in New York State: Finger Lakes (Water, Wine, and Waterfalls)

Does your idea of romance involve water? If so, the Finger Lakes region may be the most romantic destination in the state. Here, glassy glacial lakes reflect the sky like mirrors, while hilly vineyards rise and fall like a vast seascape.

Perfect couple activities include:

• Waterfall Hikes –Some trails weave directly behind cascading falls!
• Lakeside Picnics –What’s more romantic than finger foods by the Finger Lakes?
• Sunset Paddling –Picture it: effortlessly slicing through the glassy surface, dipping your oar in the orange and red water, molten drops dripping from your paddle — it’s like you’re gliding across the sky.
• Wine-Tasting Tours –Hit the Finger Lakes Wine Trail for a scenic tour of the region’s famous vineyards and wineries.

Where to Stay on Romantic Getaways in Upstate NY: Callicoon Hills (Catskills)

Planning a romantic, nature-forward getaway to Upstate New York? Your choice of lodging makes all the difference. The ideal accommodations should immerse you in the great outdoors without skimping on the creature comforts. Callicoon Hills in the Catskills captures that balance beautifully. Set on 23 acres of peaceful countryside, this boutique hotel is the perfect place to hide away with that special someone for a weekend of intentional one-on-one time in a natural setting.

Accommodations

Callicoon Hills offers multiple lodging options suited to every type of couple. Here’s a closer look:

Boarding House – Built in 1905, the Boarding House is the historic heart of Callicoon Hills. It’s perfect if you want the charm of a boutique inn and convenience to shared amenities.

Ridge Rooms – If you’re looking for peace and quiet but don’t want to sacrifice luxury, Ridge Rooms is for you. Tucked into the trees, it’s the perfect mix of posh and private.

A-Frame Cabins – Perhaps the most romantic lodging option at Callicoon Hills, these petite glamping accommodations were built with couples in mind. Immerse yourself in nature and nurture as you and your significant disappear into the pines, enjoying modern comforts like plush beds, WiFi, and electricity.

Pool House Rooms – Great for a casual getaway, the Pool House offers bright and airy guest rooms right next door to the outdoor pool and other communal areas.

Amenities Couples Love

At Callicoon Hills, you’ll enjoy access to a range of romantic amenities, including:

How to Plan the Perfect Romantic Weekend Getaway in Upstate NY

Want to make the most of your romantic getaway to upstate New York? Don’t try to cram too much into your trip. Here’s what the perfect weekend escape for two might look like:

Day 1: Arrive, explore the grounds, dinner at Conover Club, and a night around the fire pit
Day 2: Morning coffee outdoors, scenic hike on one of Callicoon’s private trails, afternoon dip in the pool, drinks at sunset
Day 3: A slow, casual breakfast followed by one last stroll among the pines

Remember, the best romantic getaways aren’t about hitting every item on your checklist; they’re about spending quality time with the one you love.

Discover More Romantic Escapes with Nook Outdoors

Looking for something else? We’ve got you covered! Upstate New York is just one example of how romantic a nature-forward getaway can be. Our curated collection of outdoor accommodations ranges the US, from the Southern Maine Coast to the beaches of the Big Island. Find your ideal romantic getaway at the link below!