Photo by Matthew Rigby Photography
When Chelsea and Alon started planning their wedding at The Ruins at Sassafras, they knew exactly what they didn't want—a day that felt rushed, overly staged, or disconnected from who they really are. As passionate ultimate frisbee players with a tight-knit community of teammates they considered family, they needed a venue that would give them space to actually be present with the people they love, not spend the entire day posing for photos.
That's exactly what drew them to The Ruins at Sassafras in New Lebanon, NY. This historic former Shaker settlement offers something increasingly rare in the Hudson Valley—a venue that prioritizes authentic connection over picture-perfect moments, with enough natural beauty and thoughtful design that the photos take care of themselves.
One of the aspects that sets The Ruins apart is how intentionally it's been restored. Every corner of the expansive estate reflects genuine care and historical significance, from the 200-year-old Shaker Chair Factory to the stone ruins framed by wildflowers. For couples who value meaning over trends, this venue delivers.
Photos by Matthew Rigby Photography
A venue for couples seeking connection and smooth coordination
The biggest challenge most couples face isn't finding beautiful backdrops—it's finding time to actually experience the day they've spent months planning. The Ruins at Sassafras addresses this directly through its thoughtful layout.
The property includes multiple distinct spaces across its grounds—the Stone House and Caretaker's Cottage for getting ready, the Rose Dwelling for ceremonies, Deere Pond with its weeping willow, the Moroccan Bar terrace for cocktails, and the Chair Factory for receptions. This separation means your day flows naturally from one moment to the next, rather than constantly rearranging the same space.
Chelsea and Alon got ready in separate buildings that gave their wedding party genuine privacy and room to breathe. The Stone House features a gorgeous wooden staircase, vintage furnishings, ornate mirrors, and a balcony overlooking mountain views between the Taconic and Berkshire ranges. The space feels more like staying at a friend's beautifully restored home than a sterile bridal suite.
This meant that the timeline wasn’t dictated by logistics, and I could document getting ready moments without feeling cramped, capture first look photos in the pine groves outside, and move seamlessly to their ceremony in the Rose Garden without any awkward waiting periods.
Photos by Matthew Rigby Photography
Getting ready spaces that support your timeline
One detail I appreciate as a photographer who's documented dozens of venues is that The Ruins at Sassafras offers genuine accommodations, not afterthought spaces. Up to 18 people can stay on-site across the Stone House, Caretaker's Cottage, and Smoke House, which transforms the entire weekend into an intimate experience.
Natural light floods through large windows, perfect for soft morning documentation. Architectural details like wooden staircases and vintage furnishings provide beautiful backdrops without feeling staged, and multiple rooms mean I can document different moments simultaneously. The balcony with wrought iron railing overlooks expansive mountain views—a stunning spot for quiet pre-ceremony moments. Behind the Stone House, a patio with trellis offers another option for portraits.
Chelsea's wedding party spent the morning moving between spaces, stepping outside for fresh air, and genuinely relaxing. That ease translates directly into more natural photos.
Photos by Matthew Rigby Photography
Ceremony and portrait locations that you can customize
The Ruins offers multiple ceremony sites, each with distinct character:
The Rose Garden sits centrally and accommodates up to 230 guests. Chelsea and Alon chose this space because it kept guests comfortable while freeing up other areas for portraits immediately after the ceremony. The intentional landscaping provides natural beauty without requiring extensive floral additions.
The Stone Ruins create a more intimate atmosphere, especially for late afternoon ceremonies lit by string lights. Inside this 200-year-old stone barn, you'll hear Sassafras Falls tumbling nearby while votive candles flicker in the walls. This space accommodates up to 150 for ceremonies or 100 for seated dining.
Deere Pond features a graceful weeping willow and mountain views for couples who want nature as their primary backdrop.
Chelsea and Alon's mid-afternoon ceremony gave us ideal light, kept guests comfortable, and meant we could use golden hour for romantic couple portraits.
Photos by Matthew Rigby Photography
Portrait sessions that don't monopolize your wedding day
Here's where my approach aligns perfectly with what The Ruins at Sassafras offers. Chelsea and Alon had a clear priority—they wanted to attend cocktail hour and actually talk with their friends and family, not disappear for an hour while guests waited.
We split their portrait session into two focused blocks:
Immediately after the ceremony (20 minutes): We stayed on the hilltop, using the buildings, Rose Garden, and mountain views behind the Moroccan Bar. This gave them formal family photos and romantic couple photos while the moment still felt fresh. Then I brought them directly to cocktail hour, where their frisbee teammates cheered as they walked in. They spent the next 45 minutes genuinely enjoying their celebration.
During golden hour (20 minutes): We explored the property's hidden corners—the long pebble path through gardens, down to the stone ruins where they had complete privacy, continuing to a bridge over a small waterfall framed by wildflowers, catching sunset with large oak trees and the Chair Factory in the background, ending at the pond with willow branches swaying overhead, and finishing halfway up the hill where long flowing grass framed them against the last golden light.
This worked because The Ruins' expansive loop trail system means you can pack tremendous variety into a short timeframe. The property's meticulous care shows in every corner—there are no "skip this part" areas, just different moods and backdrops.
Photos by Matthew Rigby Photography
Reception spaces that facilitate genuine celebration
After documenting their entrance to cocktail hour—which felt genuinely joyful because they'd actually been able to greet guests—Chelsea and Alon's celebration moved seamlessly through the evening. The expansive lawn accommodates yard games (their frisbee-loving crowd appreciated this) while the carefully manicured Moroccan terrace provided sophisticated comfort.
The Shaker Chair Factory houses receptions for up to 220 guests and offers remarkable flexibility. As the last standing Shaker chair factory in the world, this 200-year-old space brings genuine historical significance without feeling museum-like. The Moroccan Bar downstairs opens to a terrace with mountain views, perfect for after-parties or intimate evening moments.
The Ruins at Sassafras provides room for your celebration to breathe and evolve naturally. Guests can move between indoor and outdoor areas, find quiet conversation spots, or join the dance floor—whatever feels right for each person.
Photos by Matthew Rigby Photography
Practical details: How to create a wedding weekend stay and The Ruins at Sassafras pricing
Accommodations: Up to 18 guests stay on-site across three beautifully restored buildings. Sunday checkout at 3 p.m. means you're not rushing the morning after—a detail that your wedding party and family will really appreciate!
Vendor flexibility: The Ruins doesn't lock you into preferred vendor lists. You bring your own caterer, florist, and rentals, which means you can create exactly the experience you want. Carol and Jerome, the venue owners, and their coordinator Lara are known for being responsive and genuinely invested in each couple's vision.
Weekend experience: The secluded location creates an immersive celebration. Nearby Lenox offers additional accommodations, and the property provides parking for 60 cars.
Investment: Peak season venue fee begins at $24,000 and includes exclusive access to all event sites. Off-season pricing starts at $19,000. On-site accommodations start at $3,000 per night with a two-night minimum. The property requires a month-of coordinator—Lara, their in-house coordinator, is highly recommended based on couples' reviews.
Photos by Matthew Rigby Photography
Why this venue rewards thoughtful planning
The Ruins at Sassafras is not a plug-and-play venue. It's a historic property with remarkable beauty and flexibility, which means you need clear vision and careful coordination to make the most of it. For example, during the summer months you will want to lookin into portable AC or fan options for a reception in the Chair Factory. It is essential to have a photographer who understands timeline management and venue logistics, and can work seamlessly as a part of a team with your wedding coordinator or wedding planner.
My teaching background means I approach wedding days with organization and calm that helps couples stay present. I know how to read a room, anticipate what's next, and keep things moving without anyone feeling rushed. At a property like The Ruins, this matters tremendously—you have options, which is wonderful, but you also need someone who can help you navigate those options strategically.
When Chelsea and Alon told me they wanted to attend cocktail hour and didn't want to spend their whole day taking photos, I restructured their timeline to honor that. When they expressed discomfort with traditional posing, I adapted my approach to prioritize their connection over manufactured moments. This is what documentary wedding photography should do—serve your actual priorities, not just a predetermined photo list.
What makes this venue genuinely special
After photographing weddings throughout upstate New York, I have seen that what sets certain venues apart isn't just beauty, it's intention. The Ruins at Sassafras shows meticulous care in every restored building, every maintained garden path, every thoughtfully preserved historical detail.
For couples who want a wedding that feels genuinely like them, this property delivers. The combination of expansive grounds, multiple distinct spaces, and genuine historical character means you can create intimacy within grandeur, connection within celebration.
Chelsea and Alon's wedding embodied exactly what I love about both this venue and documentary photography: real moments in beautiful settings, meaningful connection prioritized over perfection, and a day that felt truly present rather than performed.
If you're considering The Ruins at Sassafras for your Hudson Valley wedding, contact me today. I'd love to talk with you about how we can approach your day in a way that keeps you comfortable, present, and genuinely enjoying the celebration you're creating.
Bonus! How I focus on building genuine comfort during portraits
The technical beauty of a venue means nothing if you feel stiff in front of the camera. I've photographed hundreds of couples, and what I've learned from my years teaching is this: people relax when they feel understood and when they can focus on each other rather than on posing.
With Chelsea and Alon, I started building that comfort long before their wedding day. Through our preliminary conversations, I learned what mattered most—their ultimate frisbee community (Chelsea was affectionately called "mom" by teammates because of how she cared for them during tournaments), their desire to be present rather than photo-focused, and their discomfort with traditional posing.
During portrait sessions, I kept them comfortable by encouraging them to focus on quality time together. I talked with them about their interests, their relationship, their team—treating them like close friends I hadn't seen in a while rather than clients I was directing. When someone feels like they're on a walk with a friend who happens to have a camera, they stop performing and start being themselves.
The Ruins at Sassafras supports this approach beautifully. There are plenty of opportunities to photograph couples separate from guests, natural corners that invite exploration, epic views that don't require awkward positioning. The property's intentional design means you can wander and discover rather than marching through a photo list.
Photo by Matthew Rigby Photography
