Canon City Events Worth Planning a Trip Around (2026 Calendar)
The 2026 Canon City events worth planning a trip around. From the Music & Blossom Festival to live music Saturdays at Whitewater Bar & Grill, here is the local's calendar.
You searched Canon City events for 2026. Here is the local's honest calendar of events worth planning a trip around.
The Quick Answer
The four Canon City events most worth planning a trip around in 2026:
- Music & Blossom Festival (early May) - parade, free concerts, and a craft fair
- Whitewater Bar & Grill Live Music Saturdays (every Saturday April 16 through October 11, 2026) - live music and events
- Santa Express Train on Royal Gorge Route Railroad (November 19 through December 30, 2026) - most dates sell out weeks or months in advance
- The Winery at Holy Cross Abbey events (dates vary) - wine and food events; check the winery's calendar
Smaller weekly events fill the rest of the calendar - check current event listings on this site or local sources before your visit.
Music & Blossom Festival (Early May)
A long-running community festival held in early May (the 2026 festival ran April 29 through May 3). It included:
- A Saturday parade on Main Street
- Free concerts and live music, including music at Blossom in the Park
- A craft fair with more than 100 vendors
- Food at the parade, and drinks and food trucks at the Cluster Duck concert on Saturday evening at Centennial Park
Why plan a trip around it: It is a free community festival that draws locals and visitors, with a family-friendly parade.
What to plan around: Book lodging early and check the festival's current schedule before you go. Make Whitewater Rooftop Social and Whitewater Bar & Grill reservations.
Whitewater Bar & Grill Live Music Saturdays
Every Saturday during open season (April 16 through October 11, 2026), Whitewater Bar & Grill hosts live music and events. Check its calendar for the lineup; some listed shows are free.
Why plan a trip around it: Shows are on the Covered Patio Stage or the Main Stage, with an outdoor patio and food and drinks on site.
Santa Express Train on Royal Gorge Route Railroad (November and December)
Holiday family train ride run by Royal Gorge Route Railroad from November 19 through December 30, 2026, with up to four departures a day. The train travels to the North Pole in the Royal Gorge, where Santa boards. Tickets include hot cocoa, cookies and a gift from Santa for every ticketed child.
Why plan a trip around it: Up to four departures a day. The railroad says most dates sell out weeks or months in advance.
What to plan around: Book early and have alternative dates in mind. Pair with a Royal Gorge Bridge winter visit (the park says it is open 365 days a year, weather permitting).
The Winery at Holy Cross Abbey Special Events
The winery holds seasonal wine and food events. Its own events page listed Wine & Wings afternoons and a Wine Run 5K in 2026, and showed no upcoming events at the time of this update.
What to plan around: Check the winery's events page and confirm details with the winery before booking travel.
Royal Gorge Bridge Special Events
The Royal Gorge Bridge & Park hosts seasonal events including:
- Live entertainment and family-friendly events from Memorial Day weekend through Labor Day weekend
Confirm specific event dates and times with the park before planning travel.
Daily Specials at Whitewater Bar & Grill and Whitewater Rooftop Social
While not events, the daily specials are worth planning a meal around:
| Day | Whitewater Rooftop Social | Whitewater Bar & Grill (in season) |
|---|---|---|
| Monday | Buy one get one | Margarita Monday (BOGO Gold Margaritas all day; karaoke at 7 PM) |
| Tuesday | Closed from Sep 1, 2026 until next season | Closed until next season ($5 domestics, $25 buckets when open) |
| Wednesday | Closed from Sep 1, 2026 until next season | Closed until next season (Tall Boy & Wing Wednesday when open: BOGO 16 oz PBR or Pacifico and $10 wings) |
| Thursday | 20% off cocktails | Locals Day (20% off your tab with a Fremont County ID) |
| Friday | $5 domestics, $25 buckets | Afternoon Club ($5 drafts, wine and wells, 3-6 PM, plus 20% off nachos) |
| Saturday | Live music on the rooftop patio, no cover charge | Live music and events |
| Sunday | $8 mimosas and bloody marys | $8 mimosas and bloody marys all day |
Seasonal Calendar
Dates below come from each organizer's own page.
| Month | What to Plan Around |
|---|---|
| April | Whitewater Bar & Grill opens April 16. |
| May | Music & Blossom Festival (April 29 through May 3 in 2026). |
| September | Whitewater Rooftop Social closes Tuesdays and Wednesdays from September 1, 2026. Pueblo Chile & Frijoles Festival, September 18-20, 2026 (downtown Pueblo). |
| October | Whitewater Bar & Grill closes for the season October 11 (back April 16, 2027). |
| November | Santa Express Train starts November 19. |
| December | Santa Express Train runs through December 30. |
| January-February | Whitewater Rooftop Social closed January 4 through February 25. Royal Gorge Bridge & Park is open 365 days a year, weather permitting. |
FAQ
What is the biggest event in Canon City?
The Music & Blossom Festival in early May is one of Canon City's longest-running annual festivals (the 2026 parade was the 88th), with a parade, free concerts and a craft fair.
When does the Santa Express Train run?
November 19 through December 30, 2026, with up to four departures a day. Royal Gorge Route Railroad operates the Santa Express Train. Most dates sell out weeks or months in advance, so book early.
Are there live music venues in Canon City?
Yes. Whitewater Bar & Grill hosts live music and events every Saturday during open season (April 16 through October 11, 2026).
Are there food festivals in Canon City?
The Music & Blossom Festival has food at the parade and food trucks at the Cluster Duck concert. Check the wineries and local listings for smaller food events.
What about the Pueblo Chile Festival?
The Pueblo Chile & Frijoles Festival happens in mid-September in downtown Pueblo (September 18 to 20 in 2026), east of Canon City. Worth a day trip from Canon City lodging.
Are events kid-friendly?
The Music & Blossom Festival has a parade and a Kidz Zone at Blossom in the Park, and the Santa Express Train gives a gift to every ticketed child. Check each event's age rules with the organizer.
What is happening in Canon City this weekend?
Check the events page on this site or local listings. Whitewater Bar & Grill live music Saturdays run during open season. Daily specials at the rooftop and Whitewater Bar & Grill run on the days they are open. Whitewater Bar & Grill and Whitewater Rooftop Social are both closed Tuesdays and Wednesdays (the Rooftop from September 1, 2026).
The Bottom Line
Canon City has steady events year-round but a few worth planning a trip around: Music & Blossom Festival (early May), Santa Express Train (November 19 to December 30), and weekly Whitewater Bar & Grill live music Saturdays. Daily specials at Whitewater Rooftop Social and Whitewater Bar & Grill add reasons to plan dinner around the day of the week. Book lodging early for the major events.
All events | Itineraries | Dining guide | Whitewater Rooftop Social | Whitewater Bar & Grill
Visit Canon City, visitcanoncity.net. Updated October 2026.
Sources
Last updated: October 11, 2026
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