October opens with plenty of ways to get out across Southeast Wisconsin: a fairground evening in West Allis, a downtown festival in Port Washington, a concert in Brookfield, or a quiet woodland morning in Wauwatosa. These 20 distinct outings mix free community choices with ticketed performances. Pick a nearby cluster and leave time to enjoy it.
Before you make plans
All times are local to Southeast Wisconsin (America/Chicago). Each numbered entry counts as one outing even when it offers several performances. Where an organizer does not publish an end time, this guide says so rather than guessing. Free admission does not cover every purchase or activity.
Book the 20-person Forest Exploration Center walk early. Theatre, studio-concert, train, and hayride capacity is limited; a ticket button is not a guarantee that your preferred seats remain. Confirm age rules, accessible seating, parking, and weather plans directly where the organizer has not published the detail you need.
Festivals & Fairs
1. Harvest Fair
Start with fairground favorites, fall activities, and live entertainment, then decide which paid attractions fit your group. Friday is an evening-only outing; Saturday and Sunday offer substantially more daytime time for families.
- Date
- Friday–Sunday, October 2–4, 2026
- Time
- Friday 5–11 p.m.; Saturday 10 a.m.–11 p.m.; Sunday 10 a.m.–6 p.m.
- Venue
- Wisconsin State Fair Park
- Address
- 640 S. 84th Street, West Allis, WI 53214
- Price
- $5 ages 12 and older; ages 11 and younger free. Parking, food, and some activities cost extra.
- Audience
- All ages.
- Tickets / registration
- Buy admission online or at the gate; optional activities may have separate tickets.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Outdoor fairground activities; check organizer updates for weather changes.
2. Milwaukee Oktoberfest
Make this your German-style food, music, and festival-games stop. The early-entry free windows can make a short visit inexpensive, but a reserved table does not replace an admission ticket.
- Date
- Friday–Sunday, October 2–4, 2026
- Time
- Friday 4–10 p.m.; Saturday 11 a.m.–10 p.m.; Sunday 11 a.m.–6 p.m.
- Venue
- Henry Maier Festival Park
- Address
- 200 N. Harbor Drive, Milwaukee, WI 53202
- Price
- $7 advance through September 30; $12 at the gate; ages 10 and younger free with an adult. Free community entry Friday 4–5 p.m. and Saturday/Sunday 11 a.m.–noon. Purchases extra.
- Audience
- All ages; alcohol for adults 21 and older with ID.
- Tickets / registration
- Admission tickets required outside free-entry periods. The event is cashless and has a clear-bag policy.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Outdoor festival; monitor organizer updates.
3. Port Washington Fall Street Festival
Combine a makers market, car show, music, and a family activity area in a walkable downtown outing. The free shuttle is a useful choice if you would rather skip searching for a space near the street closures.
- Date
- Saturday, October 3, 2026
- Time
- 11 a.m.–5 p.m.
- Venue
- Historic Franklin Street, downtown Port Washington
- Address
- Franklin Street festival district, Port Washington, WI 53074. Full-address shuttle starting points: 1180 S. Spring Street or 150 E. Seven Hills Road.
- Price
- Free admission, parking, and shuttle; food and vendor purchases extra.
- Audience
- All ages.
- Parking
- Free shuttle routes serve the two listed parking locations.
- Tickets / registration
- No advance admission reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Outdoor street festival; check conditions before leaving.
4. Beet Street
Bay View pairs a free outdoor music lineup with makers, seasonal food, and community organizations. W.I.T.C.H., Automatic, and Zed Kenzo are among the scheduled acts; the daytime block party is distinct from any separately restricted after-party.
- Date
- Saturday, October 3, 2026
- Time
- 1–7 p.m.
- Venue
- South Wentworth Avenue between Potter and Russell; Cactus Club anchor
- Address
- 2496 S. Wentworth Avenue, Milwaukee, WI 53207
- Price
- Free; food, drinks, and merchandise extra.
- Audience
- All ages for the daytime block party.
- Tickets / registration
- No advance admission reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Rain or shine; outdoor block party.
Community & Fall Fun
5. Racine First Fridays: Oktoberfest
Pair downtown shopping and food stops with a German-themed community evening. The Monument Square music program runs 5:30–8:30 p.m.; a keg-tapping ceremony and stein-holding contest add short activities between stops.
- Date
- Friday, October 2, 2026
- Time
- 4–9 p.m.; Monument Square music 5:30–8:30 p.m.
- Venue
- Downtown Racine and Monument Square
- Address
- Main Street at 5th Street, Racine, WI 53403; Downtown Racine visitor office: 425 Main Street.
- Price
- Free admission; food, beverages, and shopping extra.
- Audience
- Community outing; alcohol service requires legal drinking age and ID.
- Tickets / registration
- No advance admission reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Outdoor downtown activities with indoor business stops.
6. East Troy First Fridays: Fall Fair
A compact village-square evening brings Wire and Nail, food trucks, vendors, and family activities together. Use the chamber’s published fair hours when planning; the performer’s listing gives a later music finish, so confirm if staying specifically for the final set.
- Date
- Friday, October 2, 2026
- Time
- Fair 5–8 p.m. per the chamber; the band’s listing advertises music 5–9 p.m.
- Venue
- Village Square Park
- Address
- 2881 Main Street, East Troy, WI 53120
- Price
- Free concert listing; food, drinks, and vendor purchases extra.
- Audience
- Family and community outing.
- Tickets / registration
- No advance admission reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Outdoor village-square event; check weather updates.
7. Greenfield Fall Family Fest
Choose this short afternoon for costumes, games, carriage rides, and a trunk-or-treat atmosphere without an admission charge. The schedule includes bingo at 12:15 p.m., a costume contest at 1:15 p.m., and a pie-eating contest at 2 p.m.
- Date
- Saturday, October 3, 2026
- Time
- Noon–3 p.m.
- Venue
- Konkel Park
- Address
- 5151 W. Layton Avenue, Greenfield, WI 53220
- Price
- Free admission; purchases, if offered, separate.
- Audience
- Families and children.
- Tickets / registration
- No advance admission reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Outdoor; weather-cancellation line: 414-297-9008.
8. Lost Arts Festival
Watch traditional craft skills up close, from chair caning and spinning to bookbinding and wooden-shoe carving. Live folk music adds another reason to linger, and the museum setting gives this festival an indoor fallback.
- Date
- Saturday, October 3, 2026
- Time
- Noon–4 p.m.
- Venue
- Grohmann Museum
- Address
- 1000 N. Broadway, Milwaukee, WI 53202
- Price
- $5 general admission; $3 students/seniors; children under 12 free. Festival included. Campus is cashless.
- Audience
- All ages.
- Tickets / registration
- Regular museum admission; no separate festival reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Museum event; demonstrations move indoors if weather requires.
On Stage
9. Maybe We’ll Fly
Milwaukee Chamber Theatre explores artist Mary Nohl through a compact blend of storytelling, movement, and cello. The intimate studio arrangement places audiences on two sides of the action; choose your seats with step access in mind.
- Date
- Friday–Sunday, October 2–4, 2026
- Time
- Friday 7:30 p.m.; Saturday 4 and 8 p.m.; Sunday 2 p.m. Approximately 80 minutes, no intermission.
- Venue
- Studio Theatre, Broadway Theatre Center
- Address
- 158 N. Broadway, Milwaukee, WI 53202
- Price
- Friday adult example: $46 plus $9.63 listed tax/fees ($55.63 total). Discounts and other performance prices vary; check checkout.
- Audience
- Theatre audiences; production uses theatrical haze.
- Accessibility
- Official seating notes: Row A has no steps; Row B has a small step. Contact the box office about specific access needs.
- Tickets / registration
- Reserved tickets required; select the exact performance.
- Capacity / sales status
- Tickets offered online when checked; actual seats and access locations must be confirmed at booking.
- Weather
- Indoors.
10. Queens and Kings of Soul
A concert-style tribute celebrates the music associated with artists such as Aretha Franklin, Otis Redding, and Gladys Knight. Two Saturday performances make it possible to choose an afternoon outing or an evening show.
- Date
- Saturday, October 3, 2026
- Time
- 2 p.m. and 7 p.m.; end times not published.
- Venue
- Racine Theatre Guild
- Address
- 2519 Northwestern Avenue, Racine, WI 53404
- Price
- $20 adults; $18 seniors 62+; $15 students 21 and younger. Confirm final ticket total.
- Audience
- Music and theatre audiences.
- Tickets / registration
- Tickets required for the selected performance.
- Capacity / sales status
- No whole-performance sellout notice on the production page; check seat inventory when booking.
- Weather
- Indoors.
11. Cinematic Gold
The Wisconsin Philharmonic connects familiar John Williams film music with Tchaikovsky’s Violin Concerto, featuring Yevgeny Kutik. This is a useful entry point for someone who enjoys movie scores and wants a full orchestral afternoon.
- Date
- Sunday, October 4, 2026
- Time
- 3–5 p.m.
- Venue
- Sharon Lynne Wilson Center for the Arts
- Address
- 3270 Mitchell Park Drive, Brookfield, WI 53045
- Price
- Official ticket categories listed $18–$46; seat, eligibility, fees, and final price depend on selection.
- Audience
- Orchestral concert audience.
- Tickets / registration
- Reserved-seat tickets required.
- Capacity / sales status
- Ticket selection offered when checked; availability is performance- and seat-specific.
- Weather
- Indoors.
12. Live From Laurel Canyon: Songs and Stories of CSNY
Hear a tribute to Crosby, Stills, Nash & Young with historical context, narration, and visuals woven around the songs. This is a tribute production, not a performance by the original band.
- Date
- Saturday, October 3, 2026
- Time
- 7:30–9:30 p.m.
- Venue
- Sharon Lynne Wilson Center for the Arts
- Address
- 3270 Mitchell Park Drive, Brookfield, WI 53045
- Price
- Listed ticket range $49–$57; prices and fees can vary at checkout.
- Audience
- Folk-rock and music-history audiences.
- Tickets / registration
- Reserved-seat tickets required.
- Capacity / sales status
- Ticket selection offered when checked; confirm remaining seats directly.
- Weather
- Indoors.
Music & Art
13. Christian Sands
Choose an early or late set for a close-up piano performance drawing on jazz, gospel, classical influences, standards, and original music. The studio setting is the appeal here, so make a reservation before building the rest of your night around it.
- Date
- Friday, October 2, 2026
- Time
- 6:15–7:30 p.m. or 8:15–9:30 p.m.
- Venue
- Dawes Studio Theater, Sharon Lynne Wilson Center
- Address
- 3270 Mitchell Park Drive, Brookfield, WI 53045
- Price
- $45 listed; confirm fees and final checkout total.
- Audience
- Jazz and piano audiences.
- Tickets / registration
- Tickets required; choose the early or late set.
- Capacity / sales status
- Small studio seating; ticket selection was offered, but no seat availability is guaranteed.
- Weather
- Indoors.
14. Christopher’s Project
A free club show makes an approachable Friday-night music option, with jazz, R&B, pop, and swing in the band’s repertoire. Arrive around doors if getting into this small venue is central to your plans.
- Date
- Friday, October 2, 2026
- Time
- Show 8 p.m.; doors 7 p.m. End time not published.
- Venue
- Shank Hall
- Address
- 1434 N. Farwell Avenue, Milwaukee, WI 53202
- Price
- Free admission; drinks extra.
- Audience
- Nightlife venue; confirm age/ID policy with Shank Hall before bringing anyone under 21.
- Parking
- Venue recommends street parking; do not use neighboring private lots or block driveways.
- Tickets / registration
- No advance admission ticket advertised for this free show.
- Capacity / sales status
- Venue capacity is 300; free entry is subject to room capacity.
- Weather
- Indoors.
15. RAM Free First Friday
Visit Racine Art Museum for a free evening of hands-on art activities inspired by Hispanic Heritage Month. Make-and-take projects and a scavenger hunt offer a focused family stop; a DJ is scheduled from 5–8 p.m.
- Date
- Friday, October 2, 2026
- Time
- Activities 4–8 p.m.; museum’s extended hours 10 a.m.–8 p.m.
- Venue
- Racine Art Museum
- Address
- 441 Main Street, Racine, WI 53403
- Price
- Free.
- Audience
- All ages.
- Tickets / registration
- Drop-in program; no advance registration advertised.
- Capacity / sales status
- No sellout notice; activities and materials subject to availability.
- Weather
- Indoors.
16. Community Ofrenda at Milwaukee Art Museum
Explore a community altar created with the Mexican Folk Art Collective, and contribute a loved one’s name or a tissue-paper marigold. It is a reflective cultural stop rather than a timed performance; the free access route is specific.
- Date
- Sunday, October 4, 2026
- Time
- 10 a.m.–5 p.m.
- Venue
- Milwaukee Art Museum, community ofrenda
- Address
- 700 N. Art Museum Drive, Milwaukee, WI 53202
- Price
- Free access to the ofrenda through the East End entrance; other museum admission is separate.
- Audience
- All ages; remembrance and Día de los Muertos traditions.
- Tickets / registration
- Drop in through the specified entrance; no ofrenda reservation advertised.
- Capacity / sales status
- No sold-out notice posted on the official event page when checked; availability can change.
- Weather
- Indoors.
Outdoors & Adventures
17. East Troy Harvest Fest Trains
Ride a historic electric train between East Troy and the Elegant Farmer area, with time to explore seasonal stops. Treat the ticket as a day pass, then plan your return carefully: the final departure from the Elegant Farmer does not make a return trip.
- Date
- Saturday–Sunday, October 3–4, 2026
- Time
- First East Troy departure 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 Electric Railroad
- Address
- 2002 Church Street, East Troy, WI 53120; alternate boarding: 1545 Main Street, Mukwonago, WI 53149
- Price
- $19 adults 15+; $16.50 seniors/military; $13 children 3–14; ages 0–2 free. Add 5.5% sales tax; farm purchases/activities separate.
- Audience
- All ages.
- Tickets / registration
- Advance reservations recommended; tickets are nonrefundable day passes.
- Capacity / sales status
- Train capacity is finite; arrive early and confirm the day’s departure/return plan.
- Weather
- Train ride with outdoor boarding and farm stops; check operating updates.
18. Library Park Historic District Walking Tour
Look at Kenosha’s historic architecture with a guide who can connect the buildings to the city’s story. The meeting point is outside near the Civil War monument, not at the history-center building.
- Date
- Saturday, October 3, 2026
- Time
- 11 a.m.; typically about 90 minutes (approximately 12:30 p.m. finish).
- Venue
- Library Park; meet at Civil War Memorial/Winged Victory north of Simmons Library
- Address
- 711 59th Place, Kenosha, WI 53140 (Simmons Library address; meet outdoors north of the building).
- Price
- $10 per person.
- Audience
- People comfortable with an outdoor neighborhood walk.
- Accessibility
- Ask the organizer about route surfaces, distance, and accommodations before reserving.
- Tickets / registration
- Call 262-654-5770 to reserve.
- Capacity / sales status
- Reservations requested; remaining tour spaces are not published.
- Weather
- Outdoor walking tour; confirm weather plans with the history center.
19. Night on the Farm
Take a lawn chair for Oxford Hill and Catelyn Huckstep, add a food-truck dinner, and stay for a hayride after dark. This is a special evening program rather than the farm’s normal daytime admission; pony rides are not included.
- Date
- Saturday, October 3, 2026
- Time
- 5–10 p.m.
- Venue
- Green Meadows Petting Farm
- Address
- 33603 High Drive, East Troy, WI 53120
- Price
- $14 online; season-pass holders free. Food purchases extra.
- Audience
- Family and community evening; farm terrain and after-dark activities require appropriate supervision.
- Tickets / registration
- Buy special-event admission online; farm recommends advance purchase on busy special-event dates.
- Capacity / sales status
- Online tickets offered; hayrides and activity participation remain capacity-dependent.
- Weather
- Outdoor farm setting; check for weather-related changes and dress for after sunset.
20. Secrets of the Autumn Woods
Slow down with a guided look at the forest’s changing textures, fungi, and trees. The small group makes this a quieter alternative to a fall festival—and the one outing in this list with an explicitly published 20-person limit.
- Date
- Sunday, October 4, 2026
- Time
- 9–10:30 a.m.
- Venue
- Forest Exploration Center
- Address
- 1800 Forest Exploration Drive, Wauwatosa, WI 53226
- Price
- Free; registration required.
- Audience
- Nature enthusiasts; contact the organizer about suitability and accommodations for your group.
- Accessibility
- The center has accessible trailhead parking and a compacted crushed-stone trail; natural obstructions can occur. No restrooms or drinking water on site.
- Tickets / registration
- Register each participant individually through the official event page.
- Capacity / sales status
- Limited to 20 participants; check registration before traveling.
- Weather
- Outdoor woodland program; conditions may change.
A practical way to choose
For a budget-friendly family afternoon, compare Greenfield’s three-hour fest, Beet Street’s free music-and-makers block party, and Port Washington’s downtown festival. For a rainy-day alternative, look at the museum programs or reserve a theatre seat. Racine’s Friday downtown celebration and RAM program can be paired without another long drive.
Use each event’s official link for current tickets, access arrangements, and last-minute changes. This guide was checked on September 30; it cannot reserve a space or promise that conditions will stay the same through Sunday.