A Colorful Fall Wedding at Chaparral Ranch in Aspen, Colorado

When it came time for Madeline Eskind, a senior product specialist at Twitter, and William Litvack, co-founder and CEO of SquadUp, to pick a destination wedding location, there was no question: Aspen, Colorado.

Madeline and William, who grew up in Nashville and Los Angeles, respectively, both vacationed in Aspen in their childhoods. After meeting in college at Duke University, they both discovered their mutual love of skiing. They began taking trips to Aspen a few times a year as a couple, so it was an easy decision to pick the Colorado town for their September celebration.

“We wanted to play up the autumn colors in Aspen and wanted the whole experience to be joyous, festive, and personal,” Madeline explains. That, however, is easier said than done when your guest list includes inviting 300 people to a remote mountain town, so she and William hired planner Kate Ryan of Gold Leaf Event Design & Production to pull off the festivities. “A wedding of this scale requires a lot of moving pieces, but ultimately it was worth all of the thought that we poured in,” Madeline says. “Kate was amazing and our savior so many times.”

A ski bunny motif tied the entire celebration together, from the escort cards—ski passes!—to the venue—Chaparral Ranch—and the bluegrass band that played Earth Wind and Fire’s “September" as a nod to their September date. Bites, like seared elk loin and bruschetta bar, came from Caribou Club, and the wedding cake featured the bark of an Aspen tree with the couple's initials "carved" in icing. There were nods to the couple’s non-Colorado background too: The dance party space was modeled into a replica of the Duke University bar where they met, Shooters II, and they even served Blue Devil shots, the signature drink of the haunt.

“The ranch was absolutely stunning and the perfect blend of Nashville and Los Angeles: rustic yet upscale,” Madeline says. “We wanted everyone to have fun, so we tried to set the tone by having a more casual dress code and upbeat music.”

Read on for all the details of Madeline and William's rustic-modern wedding celebration, as planned by Gold Leaf Events and photographed by Rachel Havel.

After trying on several dresses but not finding “the one,” Madeline opted for a different route, taking her favorite parts of all the dresses she looked at and designing her own with Cristina Ottaviano. “I got so particular about what I was looking for, I knew I had to get it made,” Madeline says of her white, fitted, cowl-back gown. “Cristina was an absolute dream and made the dress precisely for my body.” She paired the dress with a veil by Cristina and a pair of flower stud diamond earrings from Martin Katz.

William donned a custom three-piece suit made by his family friend, David August. His look included an orange pocket square—a pop of color that coordinated with the rest of the day's design.

Madeline and William took their first vacation as a couple to Aspen, so it was no surprise that the destination was the perfect blend of modern and rustic for their destination wedding.

“A few friends and I put together a fall color palette and then everyone started buying dresses within those colors,” Madeline says of her large bridal party. To create some cohesiveness, she gifted each woman a Montunas bag.

The groomsmen all wore navy suits to coordinate with the fall-inspired colors of the bridesmaids’ dresses. They each donned an orange tie, a color that popped throughout the day in the décor, including the flowers, centerpieces, and even the cocktail hour drinks.

“Our ceremony was set behind the stables, in front of a gorgeous pond where geese resided during our ceremony,” Madeline says of the decor. “Premier Party Rentals built a custom beetle wood aisle for the processional.”

As a bluegrass band played, William walked down with his parents, Shelley and Frank Litvack. His father, Frank, also officiated the ceremony.

The couple said “I do” in front of a massive arch of garden roses, wild grasses, larkspur, smilax, and Italian ruscus. “Our family is everything to us, so we made sure that they were at the center of each moment of our wedding,” Madeline says. “They were the only ones standing during the ceremony.”

 Instead of exchanging personal vows, the couple customized the ceremony by including vignettes from their experience together. They each wrote an essay about their love story and gave it to William’s father to paraphrase for the ceremony. “He was able to beautifully tie together tradition and personal stories,” Madeline says.

The newlyweds kissed before recessing down the aisle to a bluegrass rendition of Earth Wind and Fire’s “September,” a nod to the date: September 21st.

Guests munched on fresh east and west coast oysters as well as a bruschetta station from local favorite, Caribou Club. As mentioned, the couple asked their guests to dress in semi-formal attire so they could relax—and, most importantly, have a blast!— in the casual mountain setting.

Cocktail hour décor included leather seating and a custom bar overlooking the pond.

“We couldn’t resist offering orange drinks!” Madeline says of the Aperol spritz cocktails that matched their color theme.

The couple says that they had a great time designing the escort cards with Emily Baird. The escort cards were inspired by ski passes and each table was named after a ski run. 

The couple’s reception venue isn’t typically used for events—it’s the ranch’s horseback riding arena. “Gold Leaf Events’ team flipped what’s normally a horseback riding arena into a beautiful event space unique to our wedding vision,” Madeline says.

Inside, the reception décor mixed rustic and modern elements, like stacked firewood on the bar and tufted sofas in the lounge area alongside gold accents and fresh fruit.

Tables were topped with high and low arrangements filled with fall-inspired florals and fruits, including oak branches, orange tulips, free spirit roses, orange crush roses, silver dollar eucalyptus, tangerines, safflower, white dahlias, white lisianthus, blood red oranges, kumquats, and orange ranunculus.

Similar greenery hung from modern fixtures attached to the arena’s wooden rafters. To bring in more fall tones, amber water goblets and knotted hemstitched napkins graced each place setting.

Madeline loved that the centerpieces included fresh fruit like tangerines, blood oranges, and kumquats. Place cards were made of wood to further coordinate with the venue setting

As a surprise to their guests, Madeline and William opted for an upbeat first dance. They took choreography lessons at home in Los Angeles for an energetic performance to “Higher” by Jackie Wilson. “Performing our first dance was an absolute high of the evening,” the bride adds. 

Dinner included a menu of Aspen delicacies, such as heirloom tomato and burrata salad, a duet of trout amandine and seared elk loin, wild rice, and brussels sprouts. 

The open arena space allowed Gold Leaf Events to design the entire space around the dance floor so that all the tables could be a part of the celebration. That included great views of the live band, Gen8 by Elan Artists, and a special performance by Soul Train dancer Eric Redd. Madeline and William sat facing the stage at a grand head table alongside their siblings.

The couple’s four-tier wedding cake featured orange edible flowers with berries and cream filling. It was a focal point of the space, thanks to a large installation of greenery up above.

Madeline changed into a short slip dress and a customized white denim jacket—a play on her new name!—for the dance party. 

The dance party included a replica of the Duke University bar where the newlyweds met, Shooters II, as well as plenty of Blue Devil shots and music by DJ Golden. To keep with the ski theme, the couple’s honeymoon is a two-week ski trip in Switzerland and Italy.