When we think about a City Winery wedding, we picture brick walls, glowing lights, and a cozy space filled with love and laughter. Jana and Tyler’s wedding had all of that and more. From the rehearsal dinner to the last dance, the weekend felt warm, stylish, and so true to who they are as a couple.
Hi! I’m Kayce, founder and lead planner of KR Occasions. My team and I love helping couples in the Hudson Valley and Catskills create weddings that feel effortless, personal, and unforgettable. If you’re ready to bring your own vision to life (without the stress), check out our planning services and connect with us. We’d love to hear your story!
Rehearsal Dinner at City Winery
The celebrations kicked off with a rehearsal dinner at City Winery. The space has such a cool mix of rustic and industrial. Think brick walls, wood floors, iron beams, and Edison bulbs glowing overhead. It feels warm and modern all at once.
We styled the wooden farm tables with simple linens, polished flatware, and crystal glassware to keep things elegant but not stuffy. Outside, string lights twinkled above the patio while guests relaxed in Adirondack chairs with glasses of wine.
Jana looked amazing in a fitted white lace dress with sheer overlay details and pointed heels. But her wide-brim ivory cowboy hat stole the show. It was chic, western, and totally her. Tyler matched with a dark suit, bolo tie, and brown leather shoes. Guests followed their lead, mixing semi-formal with western touches, cocktail dresses, boots, bolo ties, and even a few cowboy hats.
The vibe? Industrial elegance with a playful, down-to-earth twist. Exactly how they wanted to start their City Winery wedding weekend.
Getting Ready Moments
The morning of the wedding was relaxed and full of laughter. Jana wore a lace romper with thin straps while getting ready, and her bridesmaids matched in neutral-toned loungewear with fuzzy white slippers. (The slippers were a hit.)
Her gown was sleek and modern. Strapless, fit-and-flare with a deep neckline and buttons down the back. A long veil added drama, and ivory block-heeled shoes kept her stylish and comfortable. She wore simple drop earrings, letting the dress shine.
Her bouquet was classic and romantic: all-white roses, ranunculus, and peonies with a touch of greenery. Bridesmaids carried smaller versions, tying in with their champagne dresses.
Tyler and his groomsmen kept things sharp in black suits, white shirts, and light ties. The anticipation was real, everyone knew the day ahead would be unforgettable.
Ceremony at Church of the Holy Name of Mary
The ceremony was held at the Church of the Holy Name of Mary, a beautiful Catholic church filled with tradition and history. The altar was decorated with lilies, candles, and white-and-blush florals. A rustic wooden cross draped in fabric greeted guests at the entrance, along with a sweet “Unplugged Ceremony” sign (a nice touch to keep everyone in the moment).
Jana walked down the aisle with her father, radiant in her gown and cathedral veil. Tyler waited at the altar, looking classic in his suit and black tie. Bridesmaids glowed in champagne satin dresses, groomsmen matched in black suits, and the whole group looked perfectly coordinated.
The ceremony included heartfelt Catholic traditions like vows, candle lighting, and prayers before the Virgin Mary. The first kiss as husband and wife brought cheers from family and friends.
Afterward, the couple posed outside the brick church and in front of a stone grotto with a Virgin Mary statue. These portraits honored the setting while capturing their excitement.
Portraits at City Winery
Back at City Winery, the portraits continued. Jana and Tyler posed against the brick walls and wine barrels, mixing timeless shots with playful ones.
The wedding party looked polished in their champagne dresses and black suits. Group shots were joyful and natural, like a scene from a movie. Family portraits followed, showing the love and pride that surrounded the couple.
These photos struck the perfect balance. Formal enough for a wedding album but relaxed enough to feel like them.
Cocktail Hour at City Winery
Cocktail hour was a foodie’s dream. Guests were greeted with a “Buon Appetito” seating chart before heading to the bar for bubbles, local craft beer, and signature cocktails. A pasta station with vodka sauce served in a parmesan wheel was the talk of the night (and yes, it tasted as good as it sounds).
Passed apps like lamb chops, skewers, and crostini kept everyone mingling. And instead of a traditional guest book, Jana and Tyler had vinyl records with custom labels for guests to sig —such a fun, personal keepsake.
Reception at City Winery
When it was time for the reception, the City Winery wedding space glowed. Brick walls, string lights, and tall windows set the scene. Tables were dressed with runners, greenery, and floating candles. The sweetheart table stood out with a lush garland and candles, making it both intimate and romantic.
Personal touches were everywhere: a terracotta-toned welcome sign with their names, custom cocktail signage, and a rustic cake topped with a Polaroid photo. Guests sat at long wooden tables and round tables, all tied together with greenery and candlelight.
The energy was unmatched. Toasts brought laughter and happy tears. The dance floor filled quickly, with a disco ball sparkling overhead and music keeping everyone on their feet. It was equal parts heartfelt and fun, the perfect blend for Jana and Tyler.
Searching for the perfect Catskills wedding venue? From rustic barns to elegant estates, this blog highlights some of my favorites. Read the full post to see which venue might be the dream setting for your big day.
Wrapping It Up
Jana and Tyler wanted their wedding to be timeless, joyful, and personal. From the rehearsal dinner with western flair to the heartfelt church ceremony and the glowing reception at City Winery, that vision came to life beautifully.
For us at KR Occasions, it was such a joy to plan and style the details so they could stay present and soak in every moment.
If you’re planning your own Hudson Valley or Catskills celebration, we’d love to help make it happen. Explore our services, reach out to us, and follow along on Instagram for more love stories and behind-the-scenes looks.
Vendor Team
Wedding Planner: KR Occasions
Venue: City Winery
Photography: Madison Abbey Wedding & Elopement Photography
Beauty: UpStyleLLC
Cinema: Story Box Film
Entertainment: CNT Entertainment
Florals: Wild Grown Floral Design
Rentals & Decor: Fox Haus Events
Stationery: Delivered Details
Transportation: A.N.N. Transportation, Mid-City Transit
Travel & Accommodations: Homewood Suites by Hilton New Windsor, Holiday Inn Express & Suites Montgomery NY
