Behind the Brand: Woodstock Way Hotel

Q&A with Woodstock Way Co-Owner Ryan Giuliani

Read more about our take on Woodstock Way Hotel here.

Owners Ryan Giuliani and Jesse Halliburton bought the property back in 2014 with the vision of Woodstock Way Hotel already in mind. Ryan is the owner of Mary Giuliani Catering & Events (his wife Mary is a powerhouse in her own right and one hell of a #rebelleboss!), co-owner of Shindig (a Woodstock restaurant), and was the creator of The Pennsy Food Hall in NYC (though he is no longer part of it). Jesse is the owner/principal broker of Prime Real Estate Group in New Jersey.

So while they both have past experience in development, Woodstock Way was the first time they built a hotel from the ground up.

Woodstock Way’s four touchpoints are design, hospitality, authenticity, and location and are what make the hotel so special. They hired Jenny Keenan, a friend and designer whose firm had just finished doing the interiors for The Spectator Hotel in Charleston (we detect another #rebelleboss!!) and entrusted her with bringing their design vision to life. Knowing that staff can make or break the hotel, the team is made up of people who are talented, inviting, aligned with the hotel’s values, and who continuously keep the customer experience positive.

Authenticity, in addition to finding the history-meets-modern-day balance, shines through in the nods to the arts and music culture. Music is a huge part of the Woodstock Way brand, evidenced by each room having its own collection of vinyl curated by artists and people associated with the music business. And finally, the location. This place really couldn’t be more convenient. You’re within walking distance of everything from restaurants to hiking trails but once you’re on the property in your room, it feels like you’re hidden away in the middle of the woods.

After a gorgeous stay at Woodstock Way, I asked Ryan a few more questions to get more insights about building a hotel, his thoughts on living in the Catskills region, and the hotels that inspired Woodstock Way.

The biggest takeaways from building a hotel have been:

Breathe. It is an intense process that will push your limits financially, mentally, and your spirit, but if you surround yourself with a good team and stay on schedule, the final results should turn out the way you envisioned.

Don’t have fear about your vision. During the process, people will try to change your path and vision. You must listen and learn but have stick-to-itiveness. Stay on the path.

For a guest spending the weekend at the hotel, what would you recommend for the most quintessential Woodstock experience?

In this order: breakfast at Shindig, a hike up Overlook Mountain, buy a book about Woodstock at The Golden Notebook, then lunch at Tinker Taco Lab. Follow that with an in-room massage at the hotel, pre-dinner cocktails at Early Terrible, dinner at Cucina, see a show at Levon Helm Studios, and end the night at Station Bar and Curio.

Your favorite hotel in the world? And why?

These also inspired Woodstock Way:

  • Hotel Saint Cecilia for its authentic vibe. Walking onto this property you can feel the overwhelming feeling of COOL, just like Austin. Liz Lambert and her team created a gem! 

  • Post Ranch Inn for its architecture. If you ever stay or walk the grounds of this hotel, you’ll be blown away by the structure. It’s contemporary, rustic, and elegant. The setting over the Pacific Ocean is amazing; they have created a sanctuary for the soul. We all need to stay on this property at least once in our lifetime. 

  • Sunset Marquis for the music, being anonymous, and the thrill of meeting interesting people. This hotel was home to my wife and I every time we had to travel west for business. We had nights at this hotel that are burned into my memory forever. Sunset Marquis has mastered the art of anonymity. Some of the most recognizable people feel completely comfortable staying at this hotel. They know not only will the hotel staff provide the perfect hospitality but the other guests in the hotel mind their business. It’s a beautiful thing.

Your favorite things about the Hudson Valley?

Mountains, streams, outdoor activities, artisan lifestyles, fine local food and the positive energy that rises from the land. The area is sacred and we are lucky to live here.

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10 Waterfall Way, Woodstock, NY 12498, USA

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