Dylan & Harry
Last autumn, we drove into the Catskills to photograph Dylan and Harry’s wedding at Handsome Hollow.
They brought a lot of Brooklyn with them and none of the pretense. A live band supercharged the celebration while a tattoo artist inked guests in a loft above the reception. Guests flipped through crates of vinyl on their way out. It all made sense once you met them. Unsurprisingly, the light did what October light does. People stayed outside longer than expected (cold). Harry’s mother wore an outfit made from her old kimonos (endearing).
We documented the whole day on film and moved carefully through it. It remains one that stays with us. Hopefully we’re cool enough to revisit Brooklyn with these geniuses. If Handsome Hollow caught your eye, scroll past the gallery for a closer look at the venue itself.
Enjoy.
Handsome Hollow Wedding
Venue Handsome Hollow | Florist Field Trip Flowers | Planner Every Little Details | DJ/Band Hey Now's @ Omnipop | Photographer Superlove Film | Catering Early Bird Cookery | Transport First Student | HMUA Kindred Beauty Co. | Rentals Columbia Tent Rentals
A Closer look at handsome Hollow: Wedding venue guide
Handsome Hollow is a uniquely historic Catskills wedding venue, and one I would happily return to anytime.
After photographing two weddings here, you can feel how special this land and property is almost immediately. The atmosphere carries a quiet calm, the kind that settles over the fields and forests in the Catskills and makes the entire place feel both expansive and intimate at the same time.
At the heart of Handsome Hollow is the intentionality behind the beautiful landscape you see today. Owner Kate created the venue with the idea that couples could gather with their closest people for an entire weekend in nature rather than just a single evening celebration.
Handsome Hollow Wedding Venue: Quick Facts
Location: Long Eddy, New York (Catskills)
Venue type: Historic barn + nature estate
Property size: 93 acres
Ceremony locations: 4 options
On-site lodging: 100-year-old farmhouse
Best months: September & October
The Story Behind Handsome Hollow
When Kate first discovered the property, the vision for what it would become hadn’t yet taken shape. What stood out first was simply the land itself.
“When we first found the property, we immediately felt how special the land was, though we weren’t sure what we wanted to do with it,” Kate shared. “A few years later, we had the idea to create a place where couples could gather with their closest family and friends for a full weekend in nature.”
Not long after that idea formed, Kate and her team found the barn that would eventually become the centerpiece of the venue.
“We found our nearly 300-year-old barn near Albany. It was for sale because the farmer was building a new barn. We relocated it here. I know, crazy! It was just so beautiful, we knew it was perfect.”
Relocating the historic Amish dairy barn was the first major undertaking in transforming the property. The structure was carefully deconstructed, cleaned, transported, and rebuilt on the land that now houses Handsome Hollow, all completed in under a year back in 2014.
Today the property includes:
The restored historic Amish dairy barn
A late-19th-century farmhouse
93 acres of Catskills wilderness including fields, forests, creeks, and mountain views
The result is a wedding venue that feels both historic and deeply connected to the surrounding landscape.
What Makes Handsome Hollow Unique Among Catskills Wedding Venues
There are many beautiful wedding venues in the Catskills, but Handsome Hollow stands apart because of its scale and privacy.
“The scale and privacy of the property make it really unique,” Kate explains. “With 93 acres of fields, forests, creeks, and mountain views, couples truly have the entire place to themselves for the weekend.”
Instead of feeling like a venue couples visit briefly for their wedding day, Handsome Hollow feels more like a private estate for the entire weekend.
The restored barn, surrounding forest, and open landscape create a setting that feels elevated but still grounded in nature. It’s the kind of place where the celebration unfolds at a slower pace: welcome gatherings on Friday evening, a wedding celebration on Saturday, and brunch with friends on Sunday morning before everyone heads home.
Ceremony Locations at Handsome Hollow
One of the most exciting aspects of planning a wedding at Handsome Hollow is choosing where your ceremony will take place. The property offers several distinct locations, each with a slightly different atmosphere.
The Fern Forest
If I had to choose a favorite ceremony site, this one would be near the top of the list.
Tucked deep in the woods, the fern forest ceremony space feels completely private. A clearing surrounded by lush greenery creates a naturally intimate setting.
Kate shares the same sentiment.
“If I had to choose, I would say the fern forest. It’s truly stunning. A completely private spot in the middle of the woods. It feels both intimate and expansive at the same time. Watching couples say their vows with the sun streaming through the trees never gets old.”
The Open Forest with Mountain Views
Another beautiful ceremony location sits in a more open forest clearing with distant views of the Catskills mountains. The light here can be particularly beautiful in the late afternoon as the ceremony begins.
Inside the Historic Barn
For couples who prefer an indoor ceremony, or for days when the weather has other plans, the historic barn itself becomes a stunning ceremony space. The tall ceilings, historic wood beams, and soft natural light make the barn feel both dramatic and welcoming.
The Stone Barn Ruins
One of the more unique ceremony locations on the property is the original stone barn ruins located just outside the restored barn. Built from stone gathered directly from the property, the ruins offer a historic and atmospheric setting that feels deeply connected to the land.
What Wedding Weekends Look Like at Handsome Hollow
One of the reasons couples are drawn to Handsome Hollow is the ability to celebrate across an entire weekend rather than compress everything into a single day.
“Our couples arrive on Friday, often with some family and friends, and get settled into the farmhouse,” Kate explains. “Many host a relaxed welcome cocktail party or dinner.”
A typical wedding weekend looks something
like this:
Friday
Couples and close family arrive
Welcome cocktails or a casual dinner
Saturday
Wedding ceremony in the afternoon
Cocktail hour outdoors
Dinner reception inside the barn
Dancing followed by a bonfire under the stars
Sunday
A casual brunch before guests head home
One of Kate’s favorite moments during these celebrations happens right after the ceremony.
“Everyone gathers outside the barn for cocktails as the sun starts to dip behind the mountains. There’s this ‘just married’ feeling of pure joy, and the whole property seems to glow in that moment.”
Rain Plans at Handsome Hollow
Weather is always a consideration for outdoor weddings, but Handsome Hollow has a beautifully built-in solution.
If rain arrives, ceremonies can move inside the barn without sacrificing atmosphere.
“The barn is full of light with high ceilings and historic wood beams,” Kate explains.
“It feels so warm and magical with lanterns lining the aisle and the sound of rain on the roof.”
Rather than feeling like a backup option, the barn ceremony space often feels just as special as the outdoor settings.
Where Guests Can Stay
When couples rent Handsome Hollow, they also gain access to the on-site 100-year-old farmhouse.
The farmhouse includes:
Three bedrooms
Accommodations for up to six guests
A complimentary two-night stay included with the venue rental
Many couples choose to host their wedding party or close family members here for the weekend.
For Dylan and Harry’s wedding, the couple also rentedThe Church Airbnbnearby as a getting-ready space. Originally built in 1902, the church features original wood paneling, stained glass windows, and soaring 30-foot ceilings.
For additional guests, several nearby lodging options are located near Long Eddy, NY:
Transportation and Guest Logistics
Because Handsome Hollow only has parking for about 40 cars near the farmhouse, many weddings coordinate transportation for guests.
Most couples arrange shuttle service to and from the venue for convenience and safety.
Two commonly used shuttle providers include:
First Student
Rolling V
Shuttles allow guests to relax and enjoy the evening without worrying about navigating rural roads late at night.
Booking Handsome Hollow for Your Wedding
One of the most notable aspects of Handsome Hollow is the level of care and attention Kate brings to every celebration hosted on the property.
When couples book the venue, their rental includes:
Exclusive use of the entire 93-acre property
A full wedding weekend rental
A two-night stay in the farmhouse
Venue support staff
No strict local noise ordinance
Access to multiple ceremony locations
Kate and her team also assist couples with many aspects of planning.
They help coordinate:
Vendor recommendations
Ceremony site selection
Seating arrangements
Rain plan logistics
Their goal is simple: to make the entire experience feel seamless and relaxed for couples and their families.
Best Months to Get Married at Handsome Hollow
Like many venues in the Catskills, fall is the most popular season for weddings at Handsome Hollow.
“September and October are especially popular because the Catskills are so beautiful in the fall,” Kate says.
Couples hoping for a peak fall date should plan to book early.
“Most couples book about a year to eighteen months in advance, especially if they’re hoping for a peak fall weekend.”
What Kate Hopes Couples Experience
At the end of the day, the goal for Handsome Hollow goes beyond simply hosting beautiful weddings.
Kate often asks couples a simple question when they first meet:
“How would you like to feel on Sunday morning after your wedding weekend?”
Most couples answer the same way.
“They want to feel relaxed, surrounded by the people they love, in a beautiful place. They want it to be unforgettable. That’s our goal too. So far, so good.”
FAQ: Getting Married at Handsome Hollow
Where is Handsome Hollow located?
Handsome Hollow is located near Long Eddy, New York in the Catskills region. The venue sits on a private 93-acre property surrounded by forests, creeks, and mountain views, making it a popular destination for Catskills weddings.
What makes Handsome Hollow unique as a wedding venue?
Handsome Hollow offers couples exclusive access to the entire property for the weekend. The venue features a restored historic Amish dairy barn, multiple outdoor ceremony locations, and a quiet natural setting that allows couples to host a full wedding weekend with family and friends.
What ceremony locations are available at Handsome Hollow?
Couples can choose from several ceremony locations on the property, including the fern forest, an open forest clearing with mountain views, the historic barn interior, and the original stone barn ruins just outside the barn.
What happens if it rains on the wedding day?
If the weather doesn’t cooperate, ceremonies can move inside the historic barn. The space features high ceilings, original wood beams, and beautiful natural light, creating a warm and intimate setting even during rain.
Is there lodging available at Handsome Hollow?
Yes. The venue includes a complimentary two-night stay in the on-site 100-year-old farmhouse, which sleeps up to six guests. Many couples also recommend nearby hotels and Airbnbs in the Long Eddy area for additional guests.
How far in advance should couples book Handsome Hollow?
Most couples book Handsome Hollow about 12–18 months in advance, especially if they hope to secure a popular fall wedding date in September or October when the Catskills foliage is at its peak.
Planning Your Handsome Hollow Wedding
For couples considering a Catskills wedding venue, Handsome Hollow offers something rare: privacy, nature, historic architecture, and a full weekend experience shared with the people who matter most.
After photographing weddings here myself, I can confidently say it’s one of the most memorable venues in the region.
If you're interested in learning more about pricing or availability, you can send an inquiry through the Handsome Hollow website, and their team typically responds within 24–48 hours.
And if you're looking for a photographer to document your wedding here, especially on film, I’d love to hear from you.
Send an inquiry and let’s make it happen.