May is when the Colorado Springs event calendar properly ignites. Farmers markets open across the city, patios go full-time, and Memorial Day weekend brings the region's biggest street festival.
The weather sweet spot is real: warm days, cool nights, green foothills, and the summer monsoon pattern hasn't started yet.
Old Colorado City's Territory Days — the Memorial Day weekend street festival with hundreds of vendors, live music, and Old West trappings — is one of the region's largest annual events and the unofficial start of Springs summer. Go early in the day; parking pressure is legendary.
Farmers markets return across the city in May and run through fall — Old Colorado City's Saturday market is the anchor, with neighborhood markets across the week. They double as free family outings with food trucks and live music.
May is the greenest the Front Range gets. It's prime season for the waterfall hikes — Seven Bridges, St. Mary's Falls, Helen Hunt Falls in North Cheyenne Cañon — while Pikes Peak itself typically still carries snow up high.
Happening right now
A three-day street festival held in Old Colorado City over Memorial Day weekend — vendor booths, live music, food, and family activities along Colorado Avenue. It's among the region's biggest annual events.
Most markets open in May and run into the fall. Old Colorado City's Saturday market is the best-known; several neighborhoods host markets on other days of the week.
The Pikes Peak Highway is open year-round, but spring access to the summit depends on weather — the top of the road can close or require checkpoints after late-season snow. Check conditions the morning you go.