The Catskills have always been a place where life is supposed to slow down. Where you can step away, breathe and reconnect. Sometimes those connections are personal. Just you, soaking in a space. Other times, they’re shared and the experience is entirely because of the person you’re with.
Think back to the last time you enjoyed something more because of who you shared it with. The way they smiled. The way they laughed. The quiet between words. Emotion has a way of bringing you closer to each other, to the moment and to what matters.
Especially when that emotion centers on one important question: Will you marry me?
“Nervouscited”: The Art of the Proposal
Planning a marriage proposal brings nervousness and excitement—and all the magic. It’s vulnerability and commitment wrapped in one extraordinary moment. A single memory designed to spark a lifetime more.
“The first thing I tell my clients is that the moment will be perfect,” says Francine Rambousek, owner of Franny’s Photography Studio in Callicoon.
Francine’s Five Words of Wisdom
1. The plan isn’t the memory.
“Will it go exactly as you planned? Probably not. But it will be perfect. Remember why you’re there and be 100% with the person you love. Sometimes the hiccups become the most memorable part—especially when your photographer captures those real, unscripted moments.”
2. Trust your planner.
“Don’t be afraid to share exactly what you’re envisioning. Planners help create something special you wouldn’t have thought possible. It’s what they do.”
3. Be yourself.
“It’s hard to act natural when you’re surprising someone—harder still when it’s the person you love with a marriage proposal. But remember: they love you for who you are. Be that.”
4. Nature sets the scene.
“This is what makes proposing in the Catskills so special. Nature is always dressed perfectly for the moment and will wrap you in it like nothing else can.”
5. Take your time.
“Whatever your schedule says, don’t be afraid to break it to stay in a moment with the one you love. Especially at sunset. The dinner reservation can wait.”
Finding Your Spot: Rustic Beauty & Personal Meaning
Finding the perfect proposal spot in the Sullivan Catskills isn’t a problem. Choosing which place matches your story—that’s where it gets beautifully complicated. There’s simply so much to choose from, and each shifts with the seasons, the light, the hour.
“This isn’t Sex and the City,” says Courtney Goldsmith, Event and Conference Service Manager at Callicoon Hills Resort. “We’re more Dirty Dancing—hundreds of quiet places where you can simply disappear into your moment.”
Callicoon Hills Resort sits on 23 acres nestled in the foothills, offering creekside corners, barn charm, terrace views and pavilion warmth. When you find your spot, you might just plan the wedding there too.
Five Catskills Spots Worth Popping the Question
The Sullivan Catskills offer escape without isolation—rustic beauty where life and landscape tell your story together. Here are Francine’s five favorite places to pop the question.
1. Ten Mile River Access
“Water in your engagement is always meaningful. The quiet flow symbolizes starting a new life together and it creates stunning photos. There’s a path down to the water at 10-Mile that I love photographing—couples walking together, side by side.”
2. Stone Arch Bridge
“The Stone Arch Bridge is stunning on its own, but the reflection of the arch in the water—that’s what makes it special. It creates the illusion of a circle. Time your engagement for spring and the cherry blossoms will take your breath away.”
3. Narrowsburg-Darbytown Bridge
“This steel arch bridge over the Delaware connects New York and Pennsylvania—chic meets scenic mountain valley. It’s walking distance to downtown Narrowsburg, where plenty of restaurants wait for that celebratory drink.”
4. Roebling’s Delaware Aqueduct
“A classic spot. The oldest existing wire suspension bridge in the country. The wood and texture photograph beautifully in any light. It’s everything an artist would love.”
5. Hawk’s Nest Lookout
“If you’ve seen Catskills promotional photos, you’ve likely seen Hawk’s Nest overlooking the Upper Delaware River Valley. For sweeping valley views where the landscape becomes the star, this is it.”
Getting the Shot: Work with a Pro
Once you know the approach and you’ve chosen the spot, it’s time to build the plan. Whether you work with a Catskills wedding planner or a talented local photographer or both, professional guidance is worth it.
“Finding a professional photographer to capture your engagement—which a good planner can help arrange—is money well spent,” explains Stephanie McDonough, Director of Sales for Callicoon Hills Resort. “They know when light is perfect at any specific spot. They also know how to make the story about you.”
A pro can spend time getting to know you, then handle all the logistics to make your proposal as smooth and stress-free as possible.
“One thing they can’t do is take the nerves away—but that’s good. Embrace the butterflies,” says Stephanie. “Planning matters, but don’t get so caught up in it that you lose sight of why you’re there.”
The Big Moment
Bring snacks. An umbrella. An open mind. Trust your partner. Be present with them and yourself. But at some point, you just have to ask.
“That feeling is the feeling that makes you float. There’s nothing like experiencing an engagement in the Catskills,” Stephanie says. “When they say yes, you’re in a place where that first beautiful memory together becomes memories you’ll revisit for the rest of your lives.”
And when they say yes, you’re likely steps from cafés and restaurants ready to welcome you. It’s important to sit, soak in the euphoria, stare at that ring, snap photos.
“One of the most magical things about getting engaged in the Sullivan Catskills is that every community is here to help make your experience everything it can be,” adds Courtney. “We all fell in love with this place too. We get it. And sharing it feels good.”
She said, “Yes!” Now Time to Celebrate
Whether you want waterfront views, fireside warmth or culinary excellence, Francine has photographed enough post-proposal celebrations to know exactly where couples gravitate when they want their first meal as an engaged couple to feel as special as the moment itself. These special Catskills eateries offer more than a table and a toast—they give couples a place to land, exhale, and let the reality of the moment settle in.
- Benji and Jake’s, Kauneonga Lake: The cocktails here photograph beautifully at sunset—boats floating across the lake in the background, drinks almost too pretty to sip. But more than that, there’s something about sitting lakeside after you’ve just gotten engaged. The water, the light, the whole vibe—it matches the feeling of floating you’re already experiencing. Order something celebratory, watch the sky change colors and just be in it together.
- La Cigogne, Narrowsburg: If wine is your love language, this is where you go. La Cigogne overlooks water with one of the most incredible wine lists in the region. The atmosphere is intimate without being stuffy—romantic in that effortless way where you can dress up or stay casual and either one feels right. The kind of place where you can linger over a bottle and recount every detail of how it all unfolded.
- Blue Fox Motel Restaurant & Bar, Narrowsburg: When the weather turns or you just want that cozy, tucked-away feeling, Blue Fox is perfect. A fire crackles in the hearth, the lighting is warm and the whole space feels like someone’s well-loved living room—if that someone happens to have excellent taste and a great cocktail program. It’s intimate, laid-back and exactly the kind of spot where you want to curl up together after a big moment.
- Kenoza Hall, Kauneonga Lake: For couples who want to really mark the occasion, Kenoza Hall brings it. Think Oysters Rockefeller, craft cocktails and a dining room that feels both elegant and welcoming. The food is exceptional, the setting is refined and there’s this sense that you’re celebrating something significant. Which, of course, you are. This is the spot when you want your engagement dinner to feel like an event in itself.
“The beauty of the Catskills is there’s no shortage of delicious places to toast your joy,” says Francine. “Anyone here can list their favorites and tell you the most scenic route to get there—plus where to go for ice cream after.”
Or before. There’s no rush. Stay in the moment.
Time moves slowly in the Sullivan Catskills. Especially when you’re in love.