May 19, 2026

Memorial Day Weekend Getaways from Looking Glass

Memorial Day weekend is almost here, and at Looking Glass, you’re already sitting in one of the best launching pads in Colorado. Mountain towns, festivals, wine country, national parks — all of it within a few hours’ drive. Here are five getaways worth considering this weekend.

Boulder: BolderBoulder and Beyond

If you’ve never done the BolderBoulder 10K on Memorial Day Monday, add it to the list. With 50,000 participants, live music along the route, and a finish inside Folsom Field, it’s less a race and more a party — costumes encouraged, competitive spirit optional. The Boulder Creek Festival runs all weekend with an artisan market, beer festival, and live music. Boulder is about an hour from Parker and absolutely worth the drive.

Colorado Springs: Territory Days

Territory Days has been Colorado’s largest street festival for 50 years, running May 23–25 in Old Colorado City. Hundreds of vendors, food trucks, live music, and that easy Western Colorado Springs vibe make it a great family outing. Tack on a morning hike at Garden of the Gods — free to enter and dramatically stunning — and you’ve got a full weekend close to home.

Palisade: Colorado’s Wine Country

About four hours west, Palisade is Colorado’s fruit and wine country, and Memorial Day weekend is peak season. The orchards are blooming, the patios are open, and Carboy Winery kicks off the holiday Friday evening with live music and sparkling wine. The wine trail connects more than a dozen tasting rooms within a few miles of each other — no rigid plan required. Small, walkable, and genuinely charming.

Great Sand Dunes: Colorado’s Most Unexpected Landscape

Three hours from Parker, Great Sand Dunes National Park is one of those places that doesn’t quite make sense until you’re standing in it — North America’s tallest dunes rising 750 feet against the Sangre de Cristo Mountains. Memorial Day weekend is peak season for Medano Creek, which creates an actual beach at the base of the dunes. Arrive before 8 a.m. to beat the crowds and note that Monday May 25th is a free entry day. The dark sky views at night are worth the drive alone.

Stay Close: The Underrated Staycation

Here’s an unpopular opinion: sometimes the best long weekend move is staying put. Parker’s backyard has plenty to fill three days. The Cherry Creek Trail connects miles of paths perfect for biking or a long family walk. Castlewood Canyon State Park is 20 minutes away with stunning canyon views and hiking for all levels. Downtown Parker has farmers markets, good food, and a pace that makes a long weekend feel like an actual rest.

The Best Part of Living in Looking Glass

One of the quieter advantages of putting down roots here is that you’re already positioned perfectly for adventure. Looking Glass is close enough to the mountains for a spontaneous Friday getaway, with a neighborhood genuinely worth coming home to when the long weekend is over. Tour new homes by Dream Finders Homes and Richmond American, starting in the $600s. Schedule a model home tour today — and have a wonderful and safe Memorial Day weekend.