A Rainy, Outdoor Celebration in an Aspen Meadow

Matthew Miller had planned a picture-perfect proposal for Orly Friedman, his girlfriend of nearly two years. He selected San Francisco’s Billy Goat Hill Park, where they had their first date; lined an area with votive candles; and even had friends stationed in bushes to snap photos and shoo away passersby. Orly happily said yes—but afterward, she admits, something didn’t feel right. “I knew it was happening,” she recalls of the less-than-surprising moment. “I didn’t feel the way that everyone looks in photos! I wasn’t having those emotions!” So after celebrating, she ran this idea by Matthew: What if they took turns proposing to each other? “I wanted us to make our own rules,” she says. In the ensuing months, they went back and forth, popping the question a total of nine times—via a customized crossword puzzle, for example, during a scavenger hunt around the San Francisco Bay Area, and while paragliding in Italy (“Marry Me?” was written in a field below). “It was a fun way to keep the excitement of that year going,” she says.

For their wedding last September, Matthew, who works in finance for a solar project developer, and Orly, the head of a lower school, invited 180 guests for a three-day event in Aspen, Colorado. “My grandparents celebrated their first wedding anniversary in Aspen, and my family has been visiting ever since,” says the bride. They enlisted Bluebird Productions to plan a weekend that kicked off with group activities—like bike rides (in the couple’s branded uniforms) and yoga sessions—before Friday night’s Shabbat meal and, on Saturday, a Western-themed rehearsal dinner. On Sunday, the couple married in a meadow—in the freezing rain! “We were always doing it outside...Plan B was ponchos and umbrellas,” Orly says with a laugh. Still, they kept their guests’ comfort in mind by serving hot apple cider, doing the “speed version” of the traditional Jewish ceremony, and planning a fun-filled tented reception. Keep reading for all the impeccable details of this couple's Colorado celebration, as captured by James x Schulze.

The ceremony and reception took place at Star Peak Meadow, a spot outside Aspen that the couple often visits when they're in town. "It is one of my favorite views," Orly says. "In the summer, I like to bike there, and in the winter, the only way to get out there is by cross-country ski."

The couple's invitation suite was created by Amber Moon Design to mimic the custom artwork they had commissioned by Karina Puente. The design featured elements from Aspen (trout and leaves) and their relationship (pelicans from a favorite vacation to Italy).

Aspen’s local flora also inspired the embroidery on Orly’s Dennis Basso gown. The custom design featured a long train that the bride says was perfect for the “wide-open mountain setting.”And as a final touch, she added an intricate belt made with white turquoise and natural pieces "meant to look like stones from the river."

Matthew wore a classic tux and bowtie by Giorgio Armani.

The bride spent time with her mother and grandmother before the ceremony.

For flowers, the bride had a vision of "something natural." Mindy Rice brought that idea to life with wildflowers, acorns, and early-fall foliage.

Matthew and Orly made sure that every detail of their day was thoughtfully executed and personalized. This included the kippahs, which were printed with their logo.The bride created the design to look like a setting sun and mountain peak using their initials (an "O" for Orly, and "M" for Matthew).

"Everyone had umbrellas and it was very dramatic," the bride recalls of the ceremony. "There was serious thunder during the ceremony, and I thought maybe we should wait to continue. But we decided to go for it in the cold rain. I don’t think our guests will forget that!"

The couple wanted to highlight the site's natural beauty, so they had Mindy Rice create an aisle of flowers that looked as if they were growing from the grass below.

The ceremony had two parts—a ketubah signing and a blessing under a chuppah. During the the first, the couple signed their ketubah as guests sang around them. The paper's cut-out motif was the center of the day's design and was used throughout other decor elements, from the invitation suite to Orly's dress.

Orly and Matthew also exchanged a few words to each other at this time. "Our rabbi asked us to prepare why were there today," she explains. "No vows, no promises."

Next, everyone moved to the actual ceremony site for the second half of the event. Orly and Matthew's relatives carried their chuppah over to act as the ceremony's focal point.

The rabbi spoke; Matthew broke the glass; and the pair shared their first kiss under the chuppah, which was made with Aspen tree trunks and pieces of the bride's mother and grandmother's wedding dresses.

The happy newlyweds!

Afterward, everyone moved over to the tent for bubbly and “savory s’mores” (a melty cheese/potato/cracker take on the original) before dinner. But first: They were encouraged to pose with the custom photo booth.

Outside the tent, Orly and Matthew set up a table to commemorate their relationship. They also asked their guests to leave messages for them to read on significant anniversaries to come.

The bride wanted a clean, artisanal aesthetic, so she went with late-summer harvest colors and mountain accents, like stacked logs that created a doorway into the dining room and doubled as table assignments. The reception decor incorporated several wooden elements, like plates and vessels. “I tried to envision what materials would feel right in the field,” Orly says.

Artist Karina Puente, who created the couple's custom ketubah, also made papel picado banners to hang from the tent's ceiling.

Farm tables were lined with more papel picado elements (this time, banners!) and topped with elegant candelabras and low arrangements of red, orange, and yellow blooms.

Again, wooden chargers and candle bases, as well as seasonal fruits, reiterated the wedding's natural setting.

The couple had three cakes by Megan Joy (the flavors were brewery chocolate, yuzu coconut, and chocolate tahini). Later that night, they served ice cream and warm skillet-baked cookies.

Orly and Matthew’s first dance was four months in the making. “We did a surprise routine to a mash-up of songs,” says the bride. “People were really surprised. It was fun and took many, many hours—about 100!—to learn. We are not naturally gifted dancers!” (Orly changed into a beaded Naeem Khan dress for their big number.)

At the end of the night, the newlyweds ran through a tunnel of light tubes to find the perfect exit for their Aspen celebration: the Ultimate Taxi. Says Orly, "It's an Aspen institution, but we'd never actually been in it!"