WHEN TO GO
Dates & times
All times are local to the venue · America/Chicago
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The Dec. 5 crawl advertises artisans at 20 galleries and showplaces, alongside shopping, live music and food and drink. Its event listing does not identify the participating locations or performers.
All times are local to the venue · America/Chicago
Jolly Days is the 142nd edition of the Waukesha Art Crawl, a series founded in 1997 by artist and entrepreneur Jeff Seymour. The December event brings the crawl back downtown, with art, shopping, music and food and drink in its advertised mix.
The organizer’s 2026 calendar lists Get Lucky Crawl #139 on March 7, The Mother of all Crawls #140 on May 2, Plein Air Art Crawl #141 on Oct. 3 and Jolly Days Crawl #142 on Dec. 5. These are separate editions, not dates in one continuous event.
That distinction matters for the December visit: the October edition’s Plein Air theme is not a Jolly Days program. The Waukesha West End Artists Association organizes the Art Crawl series to promote the local arts scene and encourage community engagement.
Further reading: Waukesha Art Crawl - Waukesha Art ↗ · About Us - Waukesha Art ↗
Waukesha Art’s general listing for Almont Gallery shows the range of media associated with the area’s gallery scene. It lists Jerry Gaffey for fused glass, silver jewelry, painted glassware and wearable art; Jennifer Alexander for ceramic art tiles; and Anna Grosch for fine-art photography.
These directory entries offer context about local makers, not confirmation that they or Almont Gallery will participate on Dec. 5. The event listing does not provide a December roster.
Further reading: ART GALLERIES - Waukesha Art ↗ · Jolly Days Art Crawl | Visit Waukesha Pewaukee ↗
The 2026 crawl is scheduled for 2 to 8 p.m.
Admission is listed as free. The event listing does not give prices for artwork, boutique purchases, food or drinks.
The listed destination is Downtown Waukesha, Waukesha, WI 53186.
The event listing states no age policy or event-specific accessibility information. Confirm directly with a participating venue or the organizer if either detail affects your plans.
Jolly Days Art Crawl | Visit Waukesha Pewaukee ↗ · Waukesha Art Crawl - Waukesha Art ↗
The event lists Downtown Waukesha, Waukesha, WI 53186, without a single entrance or street address. The event page does not give mode-specific transit directions; its map link can calculate directions from your starting point.
The South Street Parking Ramp and Transit Center Parking Ramp list free two-hour parking. Paid ramp parking is handled online; payment setup requires a name, license plate number, address and email, and the ramps use license-plate scanners. The downtown parking page cautions that street parking may be prohibited during special events.
Saturday, Dec. 5, 2026, from 2 to 8 p.m.
Yes. Admission is listed as free; prices for artwork, shopping, food and drinks are not given.
The listing advertises artisans at 20 galleries and showplaces but does not identify the December participants. General directories are not confirmation of the event roster.
Jolly Days Art Crawl | Visit Waukesha Pewaukee ↗ · ART GALLERIES - Waukesha Art ↗
The South Street and Transit Center parking ramps list free two-hour parking. Street parking may be prohibited during special events.
Downtown Waukesha, Waukesha, WI 53186
Map search by venue and address. Check the organiser’s entrance details before travelling.
Images from the linked sources. Each caption identifies the context of the image.
Event, planning and background information checked 2026-11-01 against the linked sources.