Things to Do in Waukesha & Milwaukee Counties: August 28-30, 2026Summer may be winding down, but Southeastern Wisconsin is not slowing down! From community festivals and farmers markets to live
Dated: September 5 2025
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At The Hupke Team, we don’t just help people find the right home—we celebrate the communities we live and work in. Fall in Southeastern Wisconsin brings a chill in the air, changing leaves, and one of the best traditions of the season: Oktoberfest. Whether you’re raising a stein in Milwaukee, watching dachshund races in Germantown, or enjoying pumpkin painting with the kids in Lake Geneva, there’s something for everyone.
Here’s your guide to the very best Oktoberfest celebrations across Southeastern Wisconsin in 2025:
📍 Heidelberg Park, 700 W. Lexington Blvd.
🗓️ Weekends, Sept. 5 – Oct. 5, 2025
🎟️ $5 Friday, $10 Saturday, Free Sunday
Authentic German food: Usinger’s sausage, schnitzel, spanferkel, pretzels
House-brewed beers, bierhall, outdoor seating
Live bands, folk dancing, midway for kids
Table reservations available for groups
📍 Erv’s Mug, 130 W. Ryan Road
🗓️ Sept. 6, 5–9 p.m.
🎟️ $50 (includes unlimited beer tastings + buffet)
Bavarian-style buffet with schnitzel, brats, pretzels
Unlimited local and national craft beers
Lively tented atmosphere with music
📍 St. Joseph Center Grounds, 29th & Orchard Streets
🗓️ Sept. 13, 11 a.m.–4 p.m.
Live music from Vern and the Originals & Hot Off the Grill
Lakefront Brewery beer, German wines, root beer
Hammerschlagen, cornhole, giant Jenga, bakery
Bring your own lawn chairs; no pets or outside beverages
📍 Gazebo Park, 5710 Broad St.
🗓️ Sept. 19 (3–11 p.m.) & Sept. 20 (11 a.m.–10:30 p.m.)
🎟️ Free
Beer tent and food stands
Oktoberfest games for all ages
Live music and a family-friendly atmosphere
📍 Elm Grove Village Park, 13600 Juneau Blvd.
🗓️ Sept. 19 (5–10 p.m.) & Sept. 20 (3:30–10 p.m.)
German and craft beers, wine, cider, and seltzers
Food trucks, yard games, and live music
0.5K Fun Run and “Raise Your Pint” endurance contest
📍 1150 Frame Park Drive
🗓️ Sept. 19 (5–10 p.m.) & Sept. 20 (12–10 p.m.)
🎟️ Free admission ($2 wristband for beer)
German food, beer, and music
Drone show over the Fox River
Masskrugstemmen (stein-holding) and hammerschlagen contests
Shuttles and family-friendly activities
📍 Downtown Beloit
🗓️ Sept. 20
Traditional German food and beer
Live music and festive games
Local vendors and community booths
📍 Downtown Burlington (“The Loop”)
🗓️ Sept. 20, Sept. 27, Oct. 4, 2025
Bavarian street festival with polka bands
Stein-hoisting contests and German beer
Vintage German car show (Oct. 4)
📍 Downtown Elkhart Lake
🗓️ Sept. 20
5K Wine & Beer Run/Walk
Live music and hammerschlagen
Commemorative “Elktoberfest” stein for participants
📍 Franksville Memorial Park, 9614 Northwestern Ave.
🗓️ Sept. 25–28
Lakefront Brewery Oktoberfest Tent with 30+ beers
Pig roast, food trucks, stein-hoisting
Yard games and free admission
📍 HarborPark (hosted by Rustic Road Brewing)
🗓️ Sept. 25–28
Local craft beer and food trucks
Live entertainment with lakefront views
Family-friendly games and activities
📍 N128W18780 Holy Hill Rd.
🗓️ Sept. 27–28
Dachshund dog races
Free museum access to three historic sites
Authentic German food, beer, and polka music
📍 2530 S. Howell Ave.
🗓️ Sept. 28, 12–8 p.m.
Beer blessing at 12:15 p.m.
Music by Jeff Winard & His Polka Party and New Generation Polka Band
Classic German menu: beef rouladen, sauerbraten pulled pork, bratwurst, pretzels, apple streusel
📍 520 E Wells St., Milwaukee
🗓️ Oct. 4–6
Brat-eating competition, Miss Oktoberfest contest
Wiener dog beauty pageant, cornhole tournament
German fare, beer garden, and family activities
📍 200 N Harbor Dr., Milwaukee
🗓️ Oct. 3 (4–10 p.m.), Oct. 4 (11 a.m.–10 p.m.), Oct. 5 (11 a.m.–6 p.m.)
🎟️ $12 (early bird $6 until Oct. 1) – Free entry windows Oct. 3 (4–5 p.m.) & Oct. 4 (11 a.m.–noon)
German food by Kegel’s Inn
Beer garden with Hofbräu, Paulaner, Leinenkugel’s and more
Vendor market, cultural performances, and yard games
📍 Downtown Cedarburg
🗓️ Oct. 4 (10 a.m.–8 p.m.) & Oct. 5 (10 a.m.–5 p.m.)
Oompah bands and Glockenspiel shows
Schnitzel, currywurst, sauerkraut-eating contest
Porsche car show, sheepshead tournament, spelling bee
📍 Old Falls Village Park, N96W15791 County Line Rd.
🗓️ Oct. 10 (4–9 p.m.) & Oct. 11 (12 p.m.–close)
🎟️ Free
Live polka from Die Freistadt Alte Kameraden (Oct. 10)
Dachshund and corgi races (Oct. 11)
Hammerschlagen, fish fry, hot pretzels, beer garden
📍 Broad & Main Streets
🗓️ Oct. 11–12 (Sat 11 a.m.–8 p.m.; Sun 11 a.m.–5 p.m.)
Scarecrow walk, wagon rides, pumpkin painting
Food vendors and live music
Family-friendly fall celebration
📍 Court House Square
🗓️ Oct. 19
100+ craft and food vendors
Car show, chili cook-off, kids’ zone
Live entertainment throughout the day
From lederhosen to listings, The Hupke Team knows how to celebrate Southeastern Wisconsin in style. In 2024, we proudly helped 121 families buy or sell their homes—closing over $38 million in sales. With 100+ five-star reviews and decades of combined experience, we’re not just your Realtors—we’re your neighbors, festival friends, and local experts.
Whether you’re raising a stein or raising a “For Sale” sign, we’re here to help. Prost from The Hupke Team!

All information was accurate at time of publication
Jennifer has been a trusted name in Southeastern Wisconsin real estate since 2003. With over two decades of experience, she brings a strategic, detail oriented approach to every transaction, whether i....
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