Calendar of Events - Colorado Springs Over 50

September 2020
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Events available for Registration...

Events in the month of September 2020
9/5/2020 - 9/7/2020

2020 will be the 89th annual Donkey Derby Days celebration!  It tops the list of favorite Cripple Creek events. People from all over the world descend on downtown, drawn by a chance to watch a race inspired by the town’s resident donkey herd, believed to be distant relatives of the original donkeys from the town’s Gold Rush days. Enjoy games, live entertainment, and heritage competitions!

The origins of this popular Colorado donkey festival date back to the 1930s, when local businessman Charley Lehew thought a Cripple Creek festival would attract people in the summer months. It wasn’t long before he and two business partners settled on donkey racing. Together, they built a race track, solicited advertising and arranged concessions and entertainment in time for the first-ever Donkey Derby Days festival.

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9/5/2020 - 9/7/2020

June 30, 2020— We are very pleased to announce that Colorado Springs Labor Day Lift Off will take place this Labor Day Weekend in a heavily modified form.  With this in mind, event organizers Hot Apple Productions, LLC and the Colorado Springs Sports Corporation plan to bring hot air balloons to residents across Colorado Springs with an innovative twist. “The Colorado Springs community will be able to experience early morning balloon launches while balloons fill the city skyline, launching from numerous locations around town,” said Hot Apple Productions Managing Member, Scott Appelman, “Additionally, we will have a pop up Balloon Glow, weather permitting. Locations to be determined for the upcoming Labor Day weekend”. 

The Colorado Springs Labor Day Lift Off continues a 43-year tradition of a hot air balloon event in Colorado Springs. “I am happy to see this beloved event continue to make a positive impact during this difficult time,” said Colorado Springs Labor Day Lift Off Founder, Dewey Reinhard.  

Labor Day Lift Off’s usual donut eating contest, lake events, and field activities will not take place and no vendors will be available. No events will occur at Memorial Park. 

“Our goal is to create a unique community event that allows residents to continue to enjoy the tradition of the Colorado Springs Labor Day Lift Off,” said Sports Corp President and CEO Tom Osborne.  Residents are encouraged to visit and join the event’s Facebook page for updates and the latest event information. 

Both partners are thrilled to be able to do this under the environment we are all experiencing. The Labor Day Lift off will be one of very few balloon events that will take place in the world this year. It will look different not being held at Memorial Park, but available for the community to watch with balloons launching from different locations in Colorado Springs.


Event website:

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A Family Fall Celebration

About this Event

Come join us for a Fall celebration at Bancroft Park in historic Old Colorado City. Live Music, Kids Games, Local Artisans, Food, Vendors and More! Free Admission. You don't want to miss this.

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9/15/2020 - 9/27/2020
Parade of Homes Etiquette

Parade home owners have graciously opened their doors to the general public for this event. To ensure the Parade of Homes experience is enjoyable for all, please follow these basic guidelines:

  • Large bags, purses and backpacks are not permitted in the homes.

  • Supervise your children at all times; homes are not child-proof.

  • Observe all parking signage and make sure not to block neighboring driveways.

  • Honor each builder's guidelines for shoe removal and shoe coverings.

  • No smoking, vaping, eating or drinking in or around the homes.

  • Respect all furnishings and off-limit areas, as all homes are private property.

  • Use only the outside restrooms if provided.

We encourage you to interact with the builder ambassadors at each home - they are there to answer your questions. You can also find a variety of resources regarding architects, landscapers, interior designers and more in each of the homes.

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9/18/2020 - 9/20/2020

The Holly Berry House Folk Art Festival is held annually at the Rock Ledge Ranch Historic Site in the spectacular Garden of the Gods Park.  It features the fine works of 165 juried artisans from across the United States.  You will find exquisite fine art, a unique array of fine crafts, one-of-a-kind collectibles, antiques and much, much more, complimented by food music and historic tours.  This event benefits the preservation and restoration of Rock Ledge Ranch.  Vendors are encouraged to apply by returning the jury form available by clicking on “Application For Jurying” shown below.

42nd Annual Holly Berry House Folk Art Festival
Rock Ledge Ranch Historic Site
Garden of the Gods Park
Colorado Springs, Colorado

Friday, September 18, 2020 … 12:00 pm – 6:00 pm

Saturday, September 19, 2020 … 9:00 am – 6:00 pm

Sunday, September 20, 2020 … 10:00 am – 4:00 pm

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9/19/2020 - 9/20/2020

Airstrip Attack is a half-mile side-by-side roll race and trap speed competition featuring more than two hundred of the fastest, most powerful street cars in the nation. The Pikes Peak Airstrip Attack is currently the only event in the country where participants have the opportunity to come together at a venue of this size and importance while competing for the title of the Mile High Victor. Thousands of automotive and speed enthusiasts are expected to be in attendance as dozens of the industry’s top manufacturers, personalities and performance and lifestyle organizations come out to participate, support and exhibit at the event.

Food and beverages will be available for purchase. Lunch-sized coolers are ok, but anything larger is prohibited.

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9/25/2020 - 9/27/2020

The annual Chile & Frijoles Festival, held each year the third weekend after Labor Day, is Pueblo’s harvest celebration. The festival is hosted by the Greater Pueblo Chamber of Commerce.

Every year, thousands pay homage to Pueblo’s best-loved crop: green chilies, particularly Pueblo Chile.

The event features live entertainment, street vendors, cooking competitions, and chilies, chilies, chilies! Held downtown along Union Avenue, the festival draws Pueblo residents as well as people from across the state and around the nation.

→ Chili & Salsa Showdown
→ Culinary Arts Demonstrations
→ Chihuahuas on Parade
→ Jalapeno Eating Contest
→ Frijoles Spitting Contest
→ 6 Entertainment stages with 50 local bands
→ 180 Street Vendors line the festival footprint
→ Fireworks Display Friday and Saturday Evening
→ Farmers Market, Local Dining & Shopping, & More!

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9/25/2020 - 9/27/2020

The Springs Fall Home Show is happening September 25th - 27th, 2020 at Colorado Springs Event Center. Just in time to finish up your home improvement projects for fall! See the latest in home improvement, remodeling, design, outdoor living and more. Meet with local and national vendors that can help you tackle any size project!


  • Free Admission & Parking
  • Children 12 & Under get in FREE
  • Enjoy live demonstrations, food sampling, contests/prizes and more from over 100 vendors

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Car Seat Cinema: Wonder

About this Event

Gates will open at 6pm. Check in and secure your parking spot, then be seated in our beergarden for food & drink! This week are friends at Sasquatch cookies will be there before the show giving FREE COOKIES to all show goers!

We cannot wait to "Social Safely" with you! Spots will be limited, so secure yours safely today! 

*all social distancing regulations, including masks while indoors, will be enforced!

*bathrooms are available in the Taproom and Barrel Room. Attendants will be present!

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