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Your Old Colorado City Fall: What's On the Avenue From August Through Pumpkins in the Park

August 6, 2026

The block of West Colorado Avenue between about 24th and 27th is one of those rare stretches where the same square of grass can be a farmers market at 8 a.m. and a concert stage by dinnertime. If you already live in Old Colorado City, you have probably noticed that the fall calendar does not so much fill up as double-book itself. The same venues take on second and third lives between August and Halloween. Here is how the next twelve weeks actually shape up on the ground, and where residents tend to land when the Avenue gets busy.

The Saturday that rebuilds itself

Bancroft Park is the piece of the neighborhood to watch. It was the town square when Colorado City was chartered in 1859, and it still behaves like one. Every Saturday through the summer and into fall, the OCC Farmers Market runs there from 7 a.m. to 1 p.m. with more than eighty vendors and food trucks. By late afternoon on some weekends the same lawn becomes a concert venue. The summer series wraps in early August: a free Pikes Peak Musicians Association concert on August 2, then Dina Baker and the King Stan Band live in Bancroft Park on August 4.

That means the practical resident's move in early August is to walk the market for produce and pastries, drop the bags at home, and come back at set time. Same park. Same benches. Different scene.

A note for anyone new to the market: parking on Colorado Avenue itself is essentially gone by 8:15. The blocks behind the Avenue on Cucharras and Pikes Peak fill more slowly, and the walk is a couple of minutes.

First Friday, and the doors you'd miss otherwise

The First Friday ArtWalk is a free, self-guided tour of the galleries, open studios, shops, and eateries along the Avenue, 5 to 8 p.m. Two dates worth pinning: August 7 and October 2. Live demonstrations, artists on-site, work available to buy from the wall.

This is also the night to use the ArtWalk as cover for finding the venues most residents miss until someone tips them off:

  • The Fifty-Niner. A hidden speakeasy tucked behind The Dice Guys Game Store. You walk through the game shop to get in. On August 7 the room hosts "The Fifty-Niner After Dark," a variety night that runs to comedy, burlesque, opera, and magic in the same evening.
  • Springs Ensemble Theatre. Colorado Springs artists produce intimate live theater, and they perform inside the Fifty-Niner Speakeasy itself. One address, two entirely different Friday nights depending on who is booked.
  • Michael Garman's Magic Town. The sculptural theater work of artist Michael Garman, a set of miniature communities from his life, holograms included. In October it becomes Spooky Magic Town for the season.
  • FFO Goods. Candle workshops every Friday at 5 p.m. and Sundays at 11 a.m. and 3 p.m. Pick a vessel, blend scents, pour your own.

The trick to First Friday is walking the Avenue west to east one time and east to west the next, because half the galleries face the sun on one pass and the storefronts on the other. You see different work the second lap.

October, block by block

October is when the neighborhood commits. All month long, local businesses stage the Scarecrow Days installation: storefronts across the Avenue put up one-of-a-kind scarecrows that run from silly to spectacular, and residents walk the strip to pick a favorite. It is a slow, low-key excuse to be outside for the shoulder-season light.

The month peaks on Saturday, October 24 with Pumpkins in the Park, noon to 6 p.m., free. Pumpkin patch and painting, balloon animals, face painters, tie-dye, harvest food, and admission into the seasonal Spooky Magic Town. The neighborhood association describes it as the fall counterweight to Territory Days in the spring and the Christmas Stroll in the winter, which is the useful mental model: four marquee weekends anchor the year and everything else grows around them.

One competing draw the same day, worth planning around: the Emma Crawford Coffin Races run in Manitou Springs on October 24 as well, 10 a.m. to 5 p.m., per Visit Colorado Springs. Coffin Races finish around the time Pumpkins in the Park hits its stride, so a full-day plan is realistic if you leave Manitou by four.

Fall at a glance:

Date What Where
Saturdays, 7 a.m.–1 p.m. OCC Farmers Market, 80+ vendors Bancroft Park
Aug 4 Dina Baker and the King Stan Band, summer concert Bancroft Park
Aug 7, Oct 2 First Friday ArtWalk, 5–8 p.m. Along W. Colorado Ave.
Aug 7 The Fifty-Niner After Dark Behind The Dice Guys Game Store
Oct 1–31 Scarecrow Days storefront trail Avenue-wide
Oct 24, 12–6 p.m. Pumpkins in the Park Bancroft Park & Magic Town

Where to eat when the Avenue is packed

On a market Saturday or a Pumpkins in the Park weekend, walk-ins at the marquee restaurants stop being realistic by six. Residents who have lived a few blocks off the Avenue for any length of time tend to sort places by what they solve:

  • Paravicini's Italian Bistro and its upstairs sister Ristorante Di Sopra are the long-standing anchors, with the Di Sopra rooftop patio catching Pikes Peak views on the second story. Reservations, always.
  • TAPAteria is fully gluten-free Spanish tapas with a private back patio, and it holds up for a quieter date night when the sidewalks out front are loud.
  • Jake and Telly's Greek Taverna takes reservations online, which sounds obvious until the ArtWalk crowd hits and it stops feeling obvious.
  • OCC Brewing and Cerberus Brewery cover the beer-and-food end without needing a plan.
  • Trails End Taproom sits in the Red Rock Shopping Center at West Colorado and 31st, with roughly forty self-pour taps and interior bike storage. It is designed to catch riders coming off the trail system to the west, and it is the easiest walk-in on a busy Avenue weekend precisely because it is a block off the main strip.
  • Front Range Barbeque runs live music alongside the smoker.
  • Mother Muff's does early cocktails and late breakfast, in that order.
  • Pizzeria Rustica for Neapolitan wood-fired.
  • Colorado City Creamery for the classic post-dinner walk, made daily on site.

For a morning that isn't the market: La Baguette for pastry and soup, or Mountain Man Nut & Fruit Co. to load up a snack bag before Red Rock Canyon.

The five-minute detour

Something that gets underestimated by residents who moved in from farther east: Red Rock Canyon Open Space is 789 acres and it is essentially at the west end of the neighborhood, acquired by the City of Colorado Springs in 2003. The bulk of the acreage is designated passive recreation, hiking, climbing, cycling, and horseback riding included. On the days the Avenue is standing room only, walking or biking in from a Red Rock trailhead is often faster than trying to park.

Small shops that reward a slow lap

If you have out-of-town guests coming for the fall weekends, the shopping stops that consistently earn a second visit from residents:

  • Squash Blossom for fine art, jewelry, bronze sculpture, and home pieces from regional and international artists.
  • Stella & Beau for a curated mix of clothing, jewelry, and gifts.
  • EllyBLUE for a lifestyle boutique with women's fashion and home décor.
  • MatchBox Candle Co. for hand-poured, locally sourced wax.

None of these need an appointment. All of them get quieter about an hour before close, which is the resident's window.

When you want a local read on more than events

Old Colorado City was voted Gold for Best Neighborhood in the local Best Of, and the reason shows up in months like October: a walkable historic district that programs itself around the people who actually live in it, not just the ones who visit. If you have been in the neighborhood a while and are starting to think about what your block has done for value, or you have friends asking what it is really like to live off the Avenue year-round, Kap|Lyons is happy to talk through it over coffee. Schedule a Free Consultation whenever the fall calendar gives you an hour back.

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