Oktoberfests

1. Brooktoberfest

OCT. 1 | BROOKFIELD 

This will be the second year Brookfield is hosting Brooktoberfest for one fun-packed day. Try your hand at a beer stein holding contest, enjoy the polka music and dancing and watch the dachshund races. Along with various local food vendors, this year a local non-profit is hosting a beer fry. 

2. Happy Day Farmhaus Oktoberfest

OCT. 2 | GERMANTOWN

Join the citizens of Germantown at Happy Day Farmhaus for live music, food and games like bags and a German favorite, Hammerschlagen where you hammer nails in to a stump. There will be Oktoberfest beer on tap along with brats from Old Germantown, a café, sausage shop and brewery established in 1842. Happy Day Farmhaus will also have all your natural harvest décor available for sale, like pumpkins, winter squash and corn stalks. 

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3. Oktoberfest in Cedarburg

OCT. 1-2 | CEDARBURG 

Taking place in Historic Downtown Cedarburg this event wouldn’t be the same without authentic German music, dancers and a wooden polka dance floor. Be sure to check out the Glockenspiel Show, the German spelling bee and the best Lederhosen contest. You’ll find German food classics like Schnitzel dinners, knodel with gravy, bratwurst, turkey legs and pretzels, just to name a few. 

4. Original Oktoberfest of Milwaukee

OCT. 1-2 | HEIDELBERG PARK

Make it to the last weekend of the Original Oktoberfest hosted by the Bavarian Bierhaus for German beer, cuisine and foods like Spanferkel, Roll Braten and rotisserie chicken. There will be tables under a pavilion that require reservation for Fridays and Saturdays along with a fee, but Sundays neither is required. They have a midway for the kids to play games and win prizes. Your furry friends are welcome on a leash as well!

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Family Festivals

5. HEAR Wisconsin’s Fall Fest

OCT. 1 | WEST ALLIS

This is HEAR Wisconsin’s 4th Annual Fall Festival. Kids love all the activities including the petting zoo, balloon maker and pumpkin decorating. HEAR Wisconsin will be there to educate you on their Mobile Audiology Clinic (MAC) bus and provide you with a free lunch and games. HEAR Wisconsin is dedicated to breaking the language and communication barriers for the hearing impaired. They’re even offering free hearing screens to anyone interested. 

6. Fall Family Fest

OCT. 1 | GREENFIELD

Get ready and get dressed up for this fun, fall family festival at Konkel Park. Take part in either the youth or adult costume contest, bingo and other games or try to win the pie eating contest. For the kiddos there are inflatables throughout the park, a haystack play area, along with pumpkin bowling, face painting and animal balloons. 

7. Fall Family Fest

OCT. 7-9 | DELAVAN

Held at Lake Lawn Resort, this Family Fall Fest could be a great weekend option for the family. This fest offers a scenic lakeside wagon ride through the resort viewing all the fall colors. Enjoy the various fun activities from sack racing, pumpkin bowling, and scarecrow decorating to a pumpkin ring toss and pumpkin painting contest. 

8. Oak Creek Fall Festival

OCT. 22 | OAK CREEK

Held in Drexel Town Square, this harvest tradition features live music, hayrides through the Emerald Preserve, and a pumpkin decorating contest. You’ll also find craft vendors, caricatures and face painting, a petting zoo, pony ride and even a costume parade! Don’t miss the Oak Creek farmers market while you’re there, because it’s the markets last day of the season. 

9. Falls Harvest Fest

OCT. 22 | MENOMONEE FALLS

This family friendly harvest festival has fun for everyone even the furry ones. Join in with live music, seasonal beers, local vendors, pumpkin paint and pet costume contest. 

10. Hallowings Pumpkin Fest

OCT. 25-30 | GREENDALE

There’s Halloween fun at Gazebo Park in historic downtown Greendale this season! Get a free pumpkin to carve and display, which will be lit until Oct. 31. Also offered is pumpkin bowling and new to most is gourd golf. You can also enter the costume contest for you and your pet. Along with live music, food and beverages, kites and spinners, there is certainly a Hallowing good time to be had. 

11. Great Pumpkin Festival

OCT. 26-29 | WHITEFISH BAY

Gather across from the Whitefish Bay Library in the little park near the fountain to see all the lit jack-o-lanterns carved by the residents themselves. During the week of the festivities, residents can pick up a pumpkin to take home and carve and then return it to be displayed through the 31st. The festival will have live music, food vendors, a beer tent, and sweet Halloween themed treats. Many picture opportunities at this fully lit jack-o-lantern display and other themed decorations. 

12. Jack-o-lantern Jubilee

OCT. 29 | DOWNTOWN MILWAUKEE

You’re encouraged to visit Red Arrow Park this season for a new Halloween themed event, presented by Waterstone Bank. Families with little ones will love this family friendly event since there’s so much for the kids. There’s story time with Wanda the Witch, bubble playtime, face painting, and they can also meet their favorite movie characters! They can also participate in a kids costume contest and you must check out the pumpkin patch. The festivities start at 10 a.m., and the first 500 guests get a free pumpkin.  

13. Fall Family Fun Fest

OCT. 29 | RACINE

Are you ready to have a howling good time at the Wustum Museum for Racine’s Fall Family Fun fest? Kids can wear costumes in order to win a costume contest and decorate pumpkins to take home. There’s also hands-on art projects, a mini pumpkin patch and a scavenger hunt. 

14. Ponyville Ciderfest

NOV. 4-6 | MILWAUKEE

For its eighth year, Ponyville Ciderfest is celebrating all things fall at the Hilton Milwaukee City Center. For lovers of the hit show “My Little Pony,” this convention is a must. There’ll be fan panels, music acts, guests from the show and activities for all ages. Also, don’t miss out on the Grand Galloping Gala.

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Craft and Vendor Fairs

15. Fall Street Festival

OCT. 8 | PORT WASHINGTON

Live music playing on two stages all day long will liven up historic downtown Port Washington. Business will move outside and other vendors will join, for a shopping experience made for everyone to enjoy. Don’t miss out on the fireworks, either, which will be shot off from Coal Dock Park. 

16. Fall Harvest Art and Craft Fair

OCT. 15 | NEW BERLIN

Sponsored by the New Berlin Junior Woman’s Club, this Art and Craft fair is on its 39th year and will be held at Ronald Reagan Elementary School. Enjoy baked goods and chili made by club members and peruse by over 120 artists and crafters. 

17. Fall Fair to Remember

OCT. 21-22 | WEST BEND

Held at the Washington County Fair Park, this is arts and crafts show is held three times a year during Spring, Fall, and Winter. At this year’s 23rd Fall Fair to Remember, there will be many vendors to visit, see their handy work, and look for gifts for this coming holiday season. Bring the kids and let them get their face professionally painted and pick what kind of balloon they want sculpted. 

18. Fall Craft Fair

NOV. 5 | OAK CREEK

The All Saints Lutheran Church has been hosting Craft Fairs for over 35 years now. Along with different arts and crafts vendors and hobbyists, there will also be a bake sale, raffle, and a luncheon for everyone to enjoy. 

19. Holiday Folk Fair

NOV. 18-20 | WEST ALLIS

Stop by the Wisconsin State Fair Park to take part in the Holiday Folk Fair, a premiere multicultural experience with music and dance, food and beverage, arts and crafts. During the Holiday Folk Fair’s 79th year, explore traditions of dozens of ethnic groups that call Milwaukee home and see how music, food and the arts all lace together.