A Winter Chic Bachelorette Guide to Aspen, Colorado

By Shayna Seid

Over The Moon Bride-To-Be Rainey Lancaster is getting married this spring, and she was tasked with planning a winter bachelorette party with her maid of honor. Since Lancaster has grown up going to Aspen, Colorado with her family, she decided it was the perfect place to host a ski weekend with 20 of her closest friends.

The group stayed between a house near town and Hotel Jerome and used the latter—which has the best espresso martini in town—as their home base for the early December weekend. And luckily for us, she’s agreed to share her #RainsLastRun itinerary with OTM, so we can plan future après-ski-filled fêtes with expert guidance.

Where They Ate

Jour De Fête, which was opened in 1988 by a French family, is the bride’s favorite breakfast spot in Aspen. “Go with the Jersey Roll breakfast sandwich or the vegetarian breakfast burrito,” she advises.

The Little Nell’s Ajax Tavern is also a crowd pleaser. Lancaster’s go-to order includes the dream-worthy truffle fries, the onion soup gratin, and the kale and quinoa caesar salad. Her crew also enjoyed the wagyu double cheeseburger and the Bloody Marys. For the best cheese fondue, head to French Alpine Bistro. “It’s called ‘liquid Swiss gold’ for a reason!” Lancaster exclaims.

Other notable mentions include the members-only spot Caribou Club and White House Tavern. “The winter wedge and their sushi-like offerings—hamachi bomb, bigeye,  crispy rice, and kampachi crunch—are incredible, but the Bomboloncini dessert—Italian donuts with espresso gelato—takes the prize,” the bride states of Caribou Club’s menu. For the latter restaurant, Lancaster notes that you really can’t go wrong with anything, but the dip duo, the Macho Salad, and the sandwiches are all amazing.

For more dining recommendations, Over The Moon also recommends Matsuhisa, Casa Tua, and Clark’s Aspen.

What They Did

On the first day, when everyone arrived, the group smartly went to go rent skis and took time to explore the town. That night, they met up at the house near downtown and had a pizza party.

The next day, people had the option to ski, explore more of Aspen, or get some work done. It’s great to give some flexibility with plans with a group that large. And after dinner, they ended the evening with some pool at Eric’s Bar.

A trip to Cloud Nine Alpine Bistro on Highlands Mountain was planned for Saturday, but sadly the mountain couldn’t open due to a lack of snow. Instead, the ladies—fully outfitted in ’80s ski gear, retro sunglasses, and wigs—danced at the base of Ajax until the sun went down.

For their last night in Colorado, what better way to say farewell than a talent show in pajamas? “All the ladies had to perform songs and routines,” Lancaster says. “The winning acts included an epic rendition of ‘Lean Wit It, Rock Wit It’ and an incredibly off-pitch performance of ‘Dreams’ by the Cranberries—which was so bad, it was good.”

Where They Shopped

Friday night was their Western-themed night at Kemo Sabe, the iconic store famous for high-end cowboy boots and hats. “We had the upstairs bar to ourselves with margaritas and country music on repeat, and the ladies were able to make custom hats branded with their initials,” the bride explains. “By the time we left, we looked like the cast of Yellowstone and it was so much fun.”

Kemo Sabe was their big shopping-focused adventure, but Lancaster notes that they also had to hit Aspen staples like Pitkin County Dry Goods, Gorsuch, and the new Miron Crosby store.

What To Pack

For a winter trip to Aspen, Lancaster recommends packing mountain-wear and pieces you can hit up après-ski in. Snow boots with traction are a must, so no one slips on ice, and knitwear for layering is essential in the cold—the bride loves this sweater from Over The Moon.

The bride’s best friend and bridesmaid Alexandra of Thistle & Briar Studio also created custom swag—sweatsuits, itineraries, bags, and more—for the trip. “When she showed me the custom, retro Aspen patch she made for me, I was floored!” Lancaster remembers. “We put them on the sweatsuits for all the ladies as a keepsake from the weekend, and it became the late night house uniform.”

Looking to create fun, personalized merch like Rainey’s for your bachelorette or wedding weekend? Make sure you follow @overthemoon for an important update soon!