26 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Monday Evening Yoga in the Park Mon 3 Aug 2026, 6:30 PM — Fitness Festival Park · 300 Second St, Castle Rock, CO 80104 · Free
Jazz in the Park Wed 5 Aug 2026, 6:30 PM — Live music Festival Park · 300 Second St, Castle Rock, CO 80104 · Free
Festival Park Farmers Market Sun 9 Aug 2026, 9:00 AM — Market Festival Park · 300 Second St, Castle Rock, CO 80104 · Free to attend
Dinner and Dueling Pianos Fri 4 Sep 2026, 6:00 PM — Live music Wide Awake Eatery · 115 Wilcox Street #Suite 120, Castle Rock, CO 80104
Kids Markets at Castle Rock Farmers Market Sat 5 Sep 2026, 8:00 AM — Market Douglas County Fairgrounds and Event Center · 500 Fairgrounds Road, Castle Rock, CO 80104
Animals Around the Rock: Batty About Castle Rock Tue 8 Sep 2026, 6:00 PM — Meetup Millhouse at Philip S. Miller Park · 1381 W. Plum Creek Pkwy, Castle Rock, CO 80109 · Not published on the town listing
Castle Rock Artfest Sat 12 Sep 2026, 9:00 AM — Art show Festival Park · 300 Second St, Castle Rock, CO 80104 · Not published on the town listing
Douglas County Supercross Sat 12 Sep 2026, 3:00 PM — Sports Douglas County Fairgrounds and Event Center · 500 Fairgrounds Rd, Castle Rock, CO 80104 · $17.85-$60.54
Festival Park Farmers Market (relocated for Artfest) Sun 13 Sep 2026, 9:00 AM — Market Douglas County Wilcox Building lawn · 301 Wilcox St, Castle Rock, CO 80104 · Free to attend
Castle Rock Artfest (day two) Sun 13 Sep 2026, 10:00 AM — Art show Festival Park / Perry Street · 300 Second St, Castle Rock, CO 80104 · Not published on the town listing
AI Generated CMAs Tue 15 Sep 2026, 11:30 AM — Market 205 Fourth St · 205 Fourth Street, Castle Rock, CO 80104
Just Between Friends Douglas County Fall & Winter Sale (General Admission) Thu 17 Sep 2026, 10:00 AM — Market Douglas County Fairgrounds Event Center · 500 Fairgrounds Rd, Castle Rock, CO 80104 · Free (general admission)
Comedy Night at Wide Awake Eatery! Featuring Bohemian Boys Comedy Thu 17 Sep 2026, 5:00 PM — Comedy Wide Awake Eatery · 115 Wilcox Street #Suite 120, Castle Rock, CO 80104
Tunes for Trails / Perks for Parks Free Concert: Ninety Percent 90s Thu 17 Sep 2026, 6:30 PM — Live music Amphitheater at Philip S. Miller Park · 1375 W. Plum Creek Pkwy, Castle Rock, CO 80109 · Free
Castle Rock Oktoberfest Sat 19 Sep 2026, 1:00 PM — Festival Wilcox Square - Historic Downtown Castle Rock · 300 Second St, Castle Rock, CO 80104 · Not published on the town listing
Walking Tour of Downtown Castle Rock Sat 26 Sep 2026, 10:30 AM — Meetup The Courtyard on Perry (tour start) · 333 Perry St, Castle Rock, CO 80104 · Free
Castle Rock Trail Festival and liveBIG Family Adventure Run Sat 3 Oct 2026, 6:00 AM — Sports Philip S. Miller Park · 1375 W. Plum Creek Pkwy, Castle Rock, CO 80109 · Registration required - price not published on the town listing
ROSEBURG, OR - CIRCUS OF HORROR Wed 7 Oct 2026, 6:00 PM — Theater Douglas County Fairgrounds and Event Center · 500 Fairgrounds Road, Castle Rock, CO 80104
Glow Dance Party - Therapeutic Recreation Fundraiser Sat 10 Oct 2026, 7:00 PM — Fitness Amphitheater at Philip S. Miller Park · 1375 W. Plum Creek Pkwy, Castle Rock, CO 80109 · Fundraiser - price not published on the town listing
Spooktacular Sat 17 Oct 2026, 1:00 PM — Spooky Philip S. Miller Park · 1375 W. Plum Creek Pkwy, Castle Rock, CO 80109 · Not published on the town listing
Fall Festival featuring Creepy Crawlies Around the Rock Sun 18 Oct 2026, 10:00 AM — Festival Festival Park · 300 Second St, Castle Rock, CO 80104 · Not published on the town listing
Book Club With J. Hoolihan Clayton Mon 19 Oct 2026, 6:00 PM — Book club Sudden Fiction Books · 221 Perry Street, Castle Rock, CO 80104
ACOTAR 6 Midnight Release Party Mon 26 Oct 2026, 9:30 PM — Meetup Sinners & Saints · 221 Perry St, Castle Rock, CO 80104 · $33.85-$49.87 · 21+
Fangtastic Festival Fri 30 Oct 2026, 11:00 AM — Spooky Festival Park · 300 Second St, Castle Rock, CO 80104 · Not published on the town listing
Free Recovery Support Group (ARP) - Every Thursday night Thu 5 Nov 2026, 7:00 PM — Support group The Church of Jesus Christ of Latter-day Saints · 950 Plum Creek Blvd, Castle Rock, CO 80104
Boozy Bookfair with Burning Through Pages Sun 8 Nov 2026, 2:00 PM — Festival 221 Perry St · 221 Perry Street, Castle Rock, CO 80104
Listings are seeded from venue and organiser calendars. See them on the map.