An early-fall weekend can mean a neighborhood art walk, a theatre seat, a farmers market bag, or a train ride between small-town stops. This September 25–27 guide brings together 20 distinct outings across Southeast Wisconsin, with free community choices alongside ticketed performances. Pick a geographic cluster instead of racing across the region: Kenosha, the Milwaukee area, Waukesha, Racine, West Bend, Hartford, and East Troy each offer a different starting point.
Before you make plans
All dates and times below are local to Southeast Wisconsin (America/Chicago). Each numbered entry is one event, even when it has several performances or activities. A published start time does not imply an unpublished end time. Free admission does not mean food, merchandise, or every activity is free.
Capacity notes describe what the official sources exposed during this check, not a live inventory guarantee. In particular, some Saturday MSO seating sections were marked limited; East Troy recommends reservations; Indeed's silent-disco headphones are first come, first served; and Zócalo's samples are available only while supplies last. Where an organizer does not publish access details, contact it about your specific needs.
Festivals & Community
1. Waukesha Oktoberfest
Frame Park becomes an easy place to combine live music, German-style festival food, and a riverside evening. Families may prefer Saturday's afternoon activities; the evening program includes a 9 p.m. laser light show on both nights.
- Date
- Friday–Saturday, September 25–26, 2026
- Time
- Friday 5–10 p.m.; Saturday noon–10 p.m.
- Venue
- Frame Park
- Address
- 1150 Frame Park Drive, Waukesha, WI 53186
- Price
- Free admission. A $2 wristband is required to purchase or consume beer; food and beverages cost extra.
- Audience
- Community and family outing; Saturday children's activities run 2–5 p.m.
- Parking
- Free shuttle from the courthouse lot, 515 W. Moreland Boulevard: Friday 5–10:30 p.m.; Saturday 3–10:30 p.m.
- Tickets / registration
- No general-admission reservation required; optional reserved tables are separate.
- Capacity / sales status
- No general-admission sellout notice posted at the time checked.
- Weather
- Outdoor event; held in rain unless severe weather changes the program.
2. Harbor Fest
Explore Milwaukee's working waterfront through science activities, performances, and harbor-focused experiences. The UWM freshwater-sciences open house and Sturgeon Fest activities make this more than a conventional street festival; optional fish sponsorship is separate from simply attending.
- Date
- Sunday, September 27, 2026
- Time
- 11 a.m.–3 p.m.
- Venue
- Harbor View Plaza and surrounding Harbor District
- Address
- 600 E. Greenfield Avenue, Milwaukee, WI 53204
- Price
- Free admission; purchases and optional sturgeon sponsorship cost extra.
- Audience
- All ages.
- Tickets / registration
- No general festival ticket listed. Arrange any optional sturgeon sponsorship through the organizer.
- Capacity / sales status
- No festival sellout notice posted. Boat rides and individual activities should not be assumed unlimited.
- Weather
- Rain or shine; waterfront activities remain subject to conditions.
3. Kenosha YMCA Fall Fest
Combine hands-on STEM activities, a craft market, family games, and community resources in one stop. The Healthy Living Expo is part of this same festival, not an additional event in the count; it ends earlier than the outdoor celebration.
- Date
- Saturday, September 26, 2026
- Time
- 10 a.m.–6 p.m.; Healthy Living Expo 10 a.m.–2 p.m.; craft market until 5 p.m.
- Venue
- Kenosha YMCA
- Address
- 7101 53rd Street, Kenosha, WI 53144
- Price
- Free admission. Children's activity tickets $1 each; bounce-house wristband $10; fun pack with wristband and six tickets $15. Food extra.
- Audience
- Families and community members.
- Parking
- YMCA parking, with overflow at Mahone Middle School and Indian Trail High School and Academy.
- Tickets / registration
- No visitor preregistration advertised; individual activities may require tickets.
- Capacity / sales status
- No admission sellout notice posted; activity participation and concessions subject to availability.
- Weather
- Indoor gym activities and outdoor festival areas; check the YMCA for weather-related changes.
4. Full Moon Festival
Spend a lakeside afternoon and evening with artisan vendors, moon-rock painting, and music from the Deadliners. This is a relaxed waterfront alternative to a reserved-seat show; bring a layer for the time after sunset.
- Date
- Saturday, September 26, 2026
- Time
- 3–10 p.m.
- Venue
- The Beach House at Simmons Island
- Address
- 5001 Simmons Island Road, Kenosha, WI 53140
- Price
- Free admission; vendor and food purchases extra.
- Audience
- Community festival; check individual activities and beverage policies with the venue.
- Tickets / registration
- Optional RSVP linked by the venue; no advance admission ticket advertised.
- Capacity / sales status
- No sold-out notice posted; the venue does not publish a general capacity guarantee.
- Weather
- Outdoor lakeside setting; check the venue's updates if conditions change.
Arts & Culture
5. Bay View Gallery Night
Build a short route through neighborhood galleries, studios, and creative businesses rather than trying to visit every stop. Lincoln Warehouse is one useful starting point, with studio and business exploration and a complimentary shuttle to Hide House.
- Date
- Friday, September 25, 2026
- Time
- Neighborhood program 5–10 p.m.; Lincoln Warehouse 5–9 p.m. Individual stops vary.
- Venue
- Bay View venues; suggested starting point: Lincoln Warehouse
- Address
- 2018 S. 1st Street, Milwaukee, WI 53207; other stops are on the organizer's event map.
- Price
- Listed Gallery Night events are free to the public; purchases extra.
- Audience
- Most stops are family-friendly; check the listing for each business.
- Accessibility
- Access differs among buildings; confirm your chosen stops directly.
- Parking
- Plan for neighborhood parking and walking; Lincoln Warehouse lists a free shuttle to Hide House.
- Tickets / registration
- No general Gallery Night registration advertised.
- Capacity / sales status
- No overall sellout notice; small studios may have room limits.
- Weather
- Indoor stops with outdoor travel between them.
6. MILK Comic Fest
Meet independent comic creators and browse work from Milwaukee and the wider Midwest. The market-hall setting makes it easy to pair a few artist conversations with a meal without committing to an all-day convention.
- Date
- Saturday, September 26, 2026
- Time
- 11 a.m.–5 p.m.
- Venue
- 3rd Street Market Hall
- Address
- 275 W. Wisconsin Avenue, Milwaukee, WI 53203
- Price
- Free admission; comics, merchandise, and food extra.
- Audience
- All ages; individual comics may have different content suitability.
- Tickets / registration
- No admission registration required by the posted event.
- Capacity / sales status
- No sold-out notice posted; individual creators' stock is limited.
- Weather
- Indoors.
7. World Oddities Expo
Browse unusual art, specimens, jewelry, and handmade objects, with demonstrations and stage programming alongside the market. This is the guide's macabre option: families should review the content before deciding whether it suits their children.
- Date
- Saturday–Sunday, September 26–27, 2026
- Time
- 11 a.m.–7 p.m. both days; VIP entry begins at 10 a.m.
- Venue
- Baird Center, Exhibit Hall A
- Address
- 400 W. Wisconsin Avenue, Milwaukee, WI 53203
- Price
- General admission listed at $20; children 12 and under free with an adult. VIP and workshops cost extra; confirm ticket coverage and checkout total.
- Audience
- Mixed-age audience; taxidermy, macabre subjects, and some performance content require parental judgment.
- Tickets / registration
- Tickets online or at the door as available; workshops require their own booking.
- Capacity / sales status
- No general-admission sold-out notice posted; workshop availability is separate and limited.
- Weather
- Indoors.
8. MOWA Educator Open House
This focused museum morning is for educators who want classroom ideas, art-making time, and a closer look at Wisconsin art. It is not a general free-admission offer for every visitor; check that you fall within the invited audience.
- Date
- Saturday, September 26, 2026
- Time
- 10 a.m.–1 p.m.
- Venue
- Museum of Wisconsin Art
- Address
- 205 Veterans Avenue, West Bend, WI 53095
- Price
- Free for the invited educator audience.
- Audience
- K–12 educators, school staff and administrators, and student teachers.
- Tickets / registration
- Advance registration encouraged through the museum.
- Capacity / sales status
- The first 50 educators may select ten free art supplies; supplies are not guaranteed for later arrivals.
- Weather
- Indoors.
Live Performances & Film
9. Gypsy at Skylight Music Theatre
Opening weekend brings the classic musical about a determined stage mother and the complicated cost of chasing show-business success. Choose an evening performance or Sunday's matinee; Saturday is the production's designated Pride Night.
- Date
- Friday–Sunday, September 25–27, 2026
- Time
- Friday and Saturday 7:30 p.m.; Sunday 2 p.m. Published running time: 2 hours 30 minutes.
- Venue
- Cabot Theatre, Broadway Theatre Center
- Address
- 158 N. Broadway, Milwaukee, WI 53202
- Price
- Sunday's official ticket page lists $50–$94; other performances and seats may differ. Check the final ticket total.
- Audience
- The theatre recommends ages 8 and older.
- Tickets / registration
- Reserved-seat tickets required; choose the correct performance on the official ticket page.
- Capacity / sales status
- No whole-performance sold-out notice on the production page; current seat inventory must be checked before travel.
- Weather
- Indoors.
10. Agatha's Almanac — Dialogues Documentary Festival
Slow down with a documentary following an independent older gardener and her relationship with the land and heirloom seeds. This single Friday screening offers a quieter counterpoint to the weekend's festivals; allow extra time for the announced post-film conversation.
- Date
- Friday, September 25, 2026
- Time
- 1 p.m.; film runs 86 minutes. Post-screening discussion has no published end time.
- Venue
- Oriental Theatre, Abele Cinema
- Address
- 2230 N. Farwell Avenue, Milwaukee, WI 53202
- Price
- $16 adults; $15 seniors 60+, students/educators and military with ID; $14 Milwaukee Film members; $9 children 12 and under.
- Audience
- Unrated documentary; review the film description for household suitability.
- Tickets / registration
- Individual ticket or applicable festival pass required; online and theatre box-office sales.
- Capacity / sales status
- Finite cinema seating; no sold-out notice on the film page when checked, but live inventory was not exposed there.
- Weather
- Indoors.
11. Milwaukee Symphony Orchestra: Kings of Soul
Byron Stripling and three featured vocalists bring classic soul repertoire to the symphony stage. It is a chance to hear familiar styles in an orchestral setting, with Saturday evening and Sunday afternoon choices.
- Date
- Saturday–Sunday, September 26–27, 2026
- Time
- Saturday 7:30 p.m.; Sunday 2:30 p.m. End time not published.
- Venue
- Bradley Symphony Center
- Address
- 212 W. Wisconsin Avenue, Milwaukee, WI 53203
- Price
- Saturday Price Level 4 balcony adult ticket displayed $52 during verification; other sections and Sunday may differ. Confirm the checkout total.
- Audience
- Concertgoers; consult MSO policies for children and accommodations.
- Tickets / registration
- Reserved-seat tickets required.
- Capacity / sales status
- Saturday box seating and Price Level 5 orchestra were marked limited; other listed areas showed availability during the check. Inventory can change.
- Weather
- Indoors.
12. Craft & Draft: A Night of Makers
Racine's Wustum grounds combine hands-on making with a changing performance lineup: cello at 6 p.m., aerial sway-pole performances at 7 and 8:30, a DJ at 7:30, and Waiting for Eddie at 9. Arrive early to explore demonstrations before settling into the music.
- Date
- Saturday, September 26, 2026
- Time
- 6–10 p.m.
- Venue
- RAM Wustum Museum of Fine Arts
- Address
- 2519 Northwestern Avenue, Racine, WI 53404
- Price
- Admission, activities, and performances free; food, drinks, artwork, and other purchases extra.
- Audience
- Community arts audience; ask the museum about any activity-specific restrictions.
- Parking
- Organizer directs visitors to RUSD Community Pathways, 2333 Northwestern Avenue, then the garden path to the entrance.
- Tickets / registration
- No required admission reservation stated on the museum's event page.
- Capacity / sales status
- No sold-out notice posted; hands-on stations may have waits or supply limits.
- Weather
- Galleries, grounds, and gardens; outdoor portions depend on conditions. Check museum updates.
Food, Markets & Nightlife
13. Southside Dining Week Preview
Preview the dining celebration with chef demonstrations, live music, and samples at Zócalo. Treat the samples as a bonus rather than a guaranteed meal: the organizer explicitly says they last only while supplies do.
- Date
- Sunday, September 27, 2026
- Time
- Noon–4 p.m.
- Venue
- Zócalo Food Truck Park
- Address
- 636 S. 6th Street, Milwaukee, WI 53204
- Price
- Free admission and samples while supplies last; additional food and drinks extra.
- Audience
- Community food-and-music event.
- Tickets / registration
- No advance general-admission ticket advertised.
- Capacity / sales status
- Samples are limited; no overall sold-out notice posted.
- Weather
- Outdoor food-truck park; confirm weather-related changes with the organizer.
14. The Low Down at Indeed Brewing
Browse the afternoon maker market, hear live music, and stay for the rooftop silent disco if that suits your evening. The two parts have different hours, so a late arrival will miss the street-market portion.
- Date
- Saturday, September 26, 2026
- Time
- Street party noon–8 p.m.; Up Top silent disco 8–10 p.m. Vendor market noon–5 p.m.
- Venue
- Indeed Brewing Milwaukee
- Address
- 530 S. 2nd Street, Milwaukee, WI 53204
- Price
- Free event admission; food, drinks, and merchandise extra.
- Audience
- Brewery and nightlife setting; verify age rules for the rooftop portion directly.
- Tickets / registration
- No general admission ticket advertised; optional RSVP linked by the organizer.
- Capacity / sales status
- Silent-disco headphones are limited and first come, first served. Do not assume a late arrival can participate.
- Weather
- Street and rooftop portions outdoors; check the brewery for weather changes.
15. Kenosha HarborMarket
Make Saturday morning a practical outing: shop produce and local foods, then leave time for handmade goods and the lakefront surroundings. The outdoor market is one event, not a separate listing for each vendor or activity.
- Date
- Saturday, September 26, 2026
- Time
- 9 a.m.–2 p.m.
- Venue
- Kenosha HarborMarket
- Address
- 2nd Avenue between 54th and 56th Streets, Kenosha, WI 53140; enter near 56th Street and 2nd Avenue.
- Price
- Free admission; purchases extra.
- Audience
- Families and shoppers of all ages.
- Parking
- Free parking is advertised; the market is on the electric streetcar route.
- Tickets / registration
- No shopper registration required.
- Capacity / sales status
- No admission sellout; vendor products can sell out before closing.
- Weather
- Outdoor market; check the organizer's current weather/opening notices.
16. West Bend Farmers' Market
Start early for a compact downtown shopping morning with growers, prepared foods, artisan goods, and entertainment. Its 11 a.m. closing time makes it a workable first stop before another Washington County outing.
- Date
- Saturday, September 26, 2026
- Time
- 7:30–11 a.m.
- Venue
- Downtown West Bend, Main Street
- Address
- Main Street from Washington Street to Hickory Street, West Bend, WI 53095; 120 N. Main Street is a downtown navigation reference, not a single admission gate.
- Price
- Free to browse; food and merchandise extra.
- Audience
- Families and shoppers; dogs must be on short leashes under the market's rules.
- Parking
- Organizer lists nearby street parking and lots along the river east of Main Street.
- Tickets / registration
- No shopper preregistration.
- Capacity / sales status
- No admission sellout; individual vendor supplies vary.
- Weather
- Rain or shine.
Outdoors & Family Adventures
17. Pike Lake Fish Fry & Live Music by Gradient
The DNR's updated listing reschedules this gathering to September 25. Pair an optional pollock dinner with music at the amphitheater, or attend the performance without buying food. Carry-ins are allowed under the posted event details.
- Date
- Friday, September 25, 2026
- Time
- 4:30–7 p.m.; dinner 4:30–6:30 p.m.; music 5–7 p.m.
- Venue
- Pike Lake Unit amphitheater, Kettle Moraine State Forest
- Address
- 3250 Kettle Moraine Road, Hartford, WI 53027
- Price
- Fish-fry plate $15; no food purchase required for music. Vehicle admission sticker required; ice cream extra.
- Audience
- Outdoor community and family outing.
- Tickets / registration
- No advance event registration stated.
- Capacity / sales status
- No sold-out notice; food availability is not guaranteed. Confirm the rescheduled date before departure.
- Weather
- Outdoors; check DNR updates for any further weather changes.
18. Havenwoods Stewardship Saturday
Trade a spectator outing for a useful morning helping staff remove invasive plants. No previous experience is needed, and tools can be borrowed. Wear long pants and closed-toe shoes and bring water; this is a working volunteer session rather than a guided leisure walk.
- Date
- Saturday, September 26, 2026
- Time
- 9–11 a.m.
- Venue
- Havenwoods State Forest
- Address
- 6141 N. Hopkins Street, Milwaukee, WI 53209
- Price
- Free volunteer activity; no vehicle admission sticker required at Havenwoods.
- Audience
- Volunteers able to take part in outdoor work; ask staff about children's participation and suitable tasks.
- Accessibility
- Discuss task and terrain accommodations with staff at 414-527-0232.
- Tickets / registration
- No preregistration requirement listed; contact the forest with group or participation questions.
- Capacity / sales status
- No sold-out notice posted; assignments depend on staff and conditions.
- Weather
- Rain or shine; dress for outdoor work.
19. Doors Open at Schlitz Audubon
Use the center's free Doors Open day to explore trails and meet educators. Short guided hikes are offered on request from 9 a.m.–3 p.m., with a raptor program from 1–2 p.m.; these are included within this single outing.
- Date
- Sunday, September 27, 2026
- Time
- 8:30 a.m.–5 p.m.; individual activities have shorter hours.
- Venue
- Schlitz Audubon Nature Center
- Address
- 1111 E. Brown Deer Road, Milwaukee, WI 53217 (Bayside)
- Price
- Free admission for this Doors Open day.
- Audience
- Families, nature enthusiasts, and visitors of all ages.
- Accessibility
- The center identifies its one-mile Central Wetlands Loop as fully accessible.
- Tickets / registration
- No general-admission registration listed; request the short guided hikes on site.
- Capacity / sales status
- No sold-out notice posted; guided activities may require waiting.
- Weather
- Indoor center plus outdoor trails; dress for conditions and confirm any activity changes.
20. East Troy Harvest Fest Trains
Ride a historic electric train between East Troy and the Elegant Farmer area with an all-day train pass. Watch the departure monitors and plan the return first: the final approximately 4 p.m. departure from Elegant Farmer does not return there.
- Date
- Saturday–Sunday, September 26–27, 2026
- Time
- First East Troy train 10 a.m.; first Elegant Farmer departure about 11 a.m. Last East Troy departure about 3 p.m.; last Elegant Farmer departure about 4 p.m.
- Venue
- East Troy Railroad Museum and Elegant Farmer depots
- Address
- 2002 Church Street, East Troy, WI 53120; alternate boarding at 1545 Main Street, Mukwonago, WI 53149.
- Price
- Day pass: ages 15+ $19; senior/military $16.50; ages 3–14 $13; ages 0–2 and members free. Convenience fee included; tax extra.
- Audience
- Families and rail-history enthusiasts.
- Accessibility
- Historic cars are not wheelchair accessible; boarding requires steps. Discuss individual needs with the museum before booking.
- Tickets / registration
- Advance reservations suggested; tickets nonrefundable. Have the confirmation number if boarding at Elegant Farmer.
- Capacity / sales status
- Finite train capacity; reservations recommended. Confirm the day's final return departure.
- Weather
- Check railroad updates; farm activities and walking between stops are outdoors.
Choose a cluster—and check before leaving
For a lower-cost Saturday, choose a morning market and one free afternoon or evening program in the same area. West Bend pairs the early market with the educator open house only for eligible educators; Kenosha offers the market, YMCA festival, and evening waterfront gathering. Racine's Craft & Draft stands on its own as a free evening arts-and-performance option.
On Sunday, Harbor Fest and the Zócalo preview offer a Milwaukee pairing, while the nature center and East Troy trains call for a more focused outing. Build in travel and parking time instead of treating the published hours as a challenge to fit everything in.
Open the official link attached to each event for current tickets, access needs, weather changes, and remaining inventory. No listing here should be read as a promise that a seat, sample, workshop place, or train departure will still be available.