September 2025 North Shore Milwaukee Events

Oktoberfest at Bavarian Bierhaus in Glendale

Milwaukee’s North Shore offers a variety of family-friendly events throughout September 2025. This guide organizes upcoming events by date and community, making it easy to plan your family adventures as summer turns to fall. Enjoy street festivals, farmers markets, outdoor concerts, and more across Shorewood, Glendale, Whitefish Bay, Fox Point, River Hills, Bayside, and Mequon/Thiensville.

Shorewood

6th Annual Shorewood Feast — Saturday, September 13, 2025 (Noon–9:00 pm) on Oakland Avenue (4200–4400 blocks). Shorewood’s signature street festival is a family-friendly foodie event with free entertainment and activities for all ages. Come for live music on multiple stages, a grand harvest dinner, local artisan vendors, and a dedicated kids’ zone with face painting, balloon artists, and a climbing wall. Don’t miss this all-day neighborhood celebration, presented by the Shorewood Business Improvement District and North Shore Bank, which promises food and fun in the heart of Shorewood.

Shorewood Farmers’ Market — Sundays, September 7, 14, 21, 28 (9:30 am–1:00 pm) at Estabrook Park (Shelter #8). This weekly open-air market runs every Sunday through late October and features local growers and bakers offering fresh vegetables, fruits, flowers, breads and more. The scenic park setting along the Milwaukee River invites families to picnic on the riverbank and enjoy live music while browsing the stalls. It’s a perfect Sunday outing to support local farmers and grab lunch from food vendors as the fall harvest comes in.

Shorewood Waters Walking Tour — Tuesday, September 23, 2025 (5:30–7:00 pm) starting at the Shorewood Public Works Yard (3801 N. Morris Blvd). Join an educational evening stroll to get a close-up look at Shorewood’s native plantings and innovative green infrastructure installations around the village. Families (and curious kids) can learn how rain gardens, bioswales, and permeable pavements help keep stormwater out of basements and local waterways. Led by the Shorewood Waters Project, this free tour offers inspiration for environmentally friendly gardening and a chance to see how Shorewood is fighting pollution with beautiful native plants. Pre-registration is required — email kaemdonlevy@gmail.com.

Glendale

Oktoberfest at Heidelberg Park — Weekends, September 5 – October 5, 2025 at the Bavarian Bierhaus (700 W. Lexington Blvd, Glendale). Milwaukee’s original Oktoberfest celebrates over 60 years of great beer, food, and music, now open Friday through Sunday all month. This festival is family-friendly during the day – there’s free parking, and a carnival midway for kids on Fridays and Saturdays with rides and games. Enjoy live polka bands, dance performances, and German fare from pretzels to schnitzel (kids’ meals available). Admission is free on Sundays (and free other days with certain apps or promotions), making it a fun way for families to experience a bit of Bavaria close to home.

Jewish High Holidays Celebration — Late September 2025 (date TBA), hosted by the City of Glendale. In honor of the Jewish High Holy Days (Rosh Hashanah and Yom Kippur), Glendale is planning a community celebration this September. Families of all faiths are welcome to join in an inclusive event recognizing the season of reflection and renewal. Past celebrations have featured music, traditional treats, and educational activities about Jewish culture and traditions. Check Glendale’s official events page for the confirmed date and details of this 75th Anniversary special event, as the city comes together to celebrate community and diversity.

Whitefish Bay

Whitefish Bay Farmers’ Market — Every Saturday, September 2025 (9 am–1 pm) at 325 E. Silver Spring Dr. (M&I Bank parking lot). The open-air Whitefish Bay Farmers’ Market runs weekly through October 25, offering a bounty of fresh and organic produce, meats, breads, flowers, honey, and more from local vendors. Saturday mornings on Silver Spring Drive become a community gathering with live music and friendly farmers happy to share cooking tips. Stroll the stalls for farm-fresh ingredients and yummy baked goods, then explore the nearby shops and cafés of Whitefish Bay’s charming downtown.

Whitefish Bay Night Market — Saturday, September 20, 2025 (5:00–9:00 pm) on Silver Spring Drive (at Consaul Commons). Cap off the market season with an evening bazaar under the stars. This special Night Market features local vendors, live music, and your favorite Whitefish Bay businesses staying open late. Families can browse artisan crafts and sweet treats, enjoy dinner from food booths, and let kids dance to the music or play in the pedestrian plaza. With a festive block-party atmosphere, the Night Market is a fun way to spend a late-summer Saturday night and support the community – don’t forget to grab a glow stick or some kettle corn for the kids!

Fox Point

Fox Point Farmers’ Market — Saturdays, September 2025 (8:00 am–12:00 pm) at 7330 N. Santa Monica Blvd. (North Shore Congregational Church parking lot). The Fox Point Farmers’ Market is a beloved weekly tradition running June 14 to October 11. Each Saturday morning, families can shop an array of Wisconsin-grown goodness – farm-fresh vegetables, fruits, herbs, cut flowers, plus local eggs, meats, honey, and bakery items. This producer-only market prides itself on friendly vendors and a community feel. Grab a coffee and let the kids pick out pumpkins or apples as fall produce arrives. Often there’s live music or kids’ activities to make your morning even more enjoyable. It’s a great way to support local farms and get to know your neighbors.

River Hills

Dog Days at Lynden Sculpture Garden — Saturday, September 20, 2025 (10:00 am–4:00 pm) at Lynden Sculpture Garden (2145 W. Brown Deer Rd, River Hills). It’s “Dog Day” at the beautiful 40-acre Lynden Garden – one day each month when families can bring their canine friends along to enjoy art and nature. Leash up your pup and explore Lynden’s outdoor sculpture collection together; dogs love romping along the trails and open fields (and kids love showing their pets the big modern art pieces!). Regular admission applies for humans (dogs get in free); just be sure to follow the garden’s pet guidelines and clean up after your pooch. September’s Dog Day is a perfect outing for the whole family – two-legged and four-legged members alike.

(Lynden Sculpture Garden also offers rotating art workshops and nature activities on weekends – check their calendar for offerings like the “Birch Bark Oil as Natural Wood Finish” workshop on Sept 27 and other family programs.)

Bayside

Bayside Fall Fest (Village Picnic & Five and Wine) — Saturday, September 20, 2025 (2:00–9:00 pm) at Bayside Village Hall and Ellsworth Park (9075 N. Regent Rd). The Village of Bayside’s annual Fall Fest is an action-packed day of community fun rolled into one big party. Start the afternoon at 2 pm with the Village Picnic – enjoy Usinger’s famous brats and hot dogs off the grill (2–6 pm) and a craft beer from the Torzala Brewing beer garden (open 2–9 pm). At 4 pm, lace up for the Bayside Five & Wine – a 5K run or 2-mile walk through the neighborhood (registration required) followed by a complimentary wine (or juice) toast at the finish. Kids will love the petting zoo, lawn games, rock climbing wall, and Touch-a-Truck activities going on throughout the afternoon. As dusk falls, spread a blanket for Movie on the Hill at 7:15 pm – a free outdoor family movie under the stars to close out the night. With live music, tasty food, and activities for all ages, Fall Fest is the don’t-miss event in Bayside this September.

Mequon/Thiensville

Thiensville Village Market — Tuesdays, September 2025 (9:00 am–2:00 pm) at Thiensville Village Park (250 Elm St, Thiensville). Every Tuesday through October 14, Thiensville’s scenic Village Park transforms into a bustling farmers market with over 70 vendors. Browse farm-fresh produce, flowers, meats, dairy, baked goods, honey, handmade crafts, and more at this vibrant market. In summer months the market features live music and storytime for kids, and while those programs wind down after August, the family-friendly atmosphere continues into September. Parents can shop for groceries or gifts while kids enjoy the park’s playground and open green space. Consistently rated one of the Milwaukee area’s best farmers markets for its variety and neighborly charm, the Thiensville Market is worth a weekday trip. Tip: Grab lunch from a food truck or bakery stall and have a picnic by the Milwaukee River which runs alongside the park.

Taste of Mequon — Saturday, September 6, 2025 (11 am–8 pm) in front of Mequon City Hall (11333 N. Cedarburg Rd). Free admission and free entertainment await at Mequon’s biggest annual street festival. Taste of Mequon brings together 20+ local restaurants and food vendors offering small plates of their best dishes – it’s a perfect chance for families to sample everything from barbecue and pizza to sushi and cupcakes. There’s live music all day on the lakefront stage, an artists’ tent with local crafts, and plenty of activities for kids (face painting, chalk art, and a kids’ cooking contest in past years). Now in its 12th year, this event draws about 12,000–15,000 attendees each year, giving it a fun, bustling atmosphere. Parking is free and plentiful nearby. Come hungry and celebrate the flavors of Mequon in this day-long community feast!

Enjoy a fantastic September with your family on the North Shore!