Territory Days is Colorado Springs' unofficial start of summer: three days over Memorial Day weekend when Old Colorado City closes Colorado Avenue to traffic and fills it with hundreds of vendors, multiple music stages, street food, and Old West flavor — gunfight reenactments included.
It's one of the region's largest annual events, and it behaves like it. The difference between a great Territory Days and a miserable one is almost entirely logistics, which is what this guide is for.
Vendor booths run the length of Old Colorado City — crafts, food, and everything in between — with live music on multiple stages and family attractions clustered near the district's side streets. Crowds build through late morning and peak in the early afternoon; the last hours of each day are noticeably calmer.
Parking is the festival's hardest problem. The neighborhood streets fill early and much of the surrounding area is permit-restricted during the event. The local playbook: arrive before mid-morning, use the event's shuttle or park-and-ride options when offered, or bike in — Midland Trail connects straight to the district.
Mornings are the family window — cooler, calmer, and short lines at the kid attractions. Strollers get difficult by noon in the central blocks. Water, hats, and sunscreen are non-negotiable at 6,000 feet in late May.
Keep planning
Territory Days runs annually over Memorial Day weekend — Saturday through Monday — in Old Colorado City. Check the current listings on this page or our events calendar for this year's hours.
Yes — admission is free. You pay for food, drinks, and whatever the vendors talk you into.
Arrive early or plan on walking. Nearby streets fill by mid-morning and parts of the neighborhood are restricted during the festival; shuttle and park-and-ride options are typically offered, and the Midland Trail makes biking in genuinely practical.
Large festival crowds, hot pavement, and gunfight reenactment noise make it a tough environment for dogs — most locals leave pets home for this one.