Milwaukee's Pumpkin Festival Season 2025: A Complete Guide

Milwaukee and its surrounding communities transform into a pumpkin paradise each fall, offering more than festivals, farms, and celebrations where families can carve jack-o-lanterns, navigate corn mazes, and celebrate the harvest season. From the spectacle of thousands of illuminated pumpkins lighting up neighborhood parks to sprawling farms with over 65 activities, the greater Milwaukee area delivers autumn experiences for every family's taste and budget. Whether you're seeking free community festivals with carved pumpkin displays numbering in the hundreds or pick-your-own adventures at working farms, this guide covers every pumpkin event worth visiting in fall 2025. The season kicks off in mid-September and reaches its crescendo throughout October, with most major festivals concentrated in the final two weeks before Halloween when jack-o-lanterns glow nightly and communities come together to celebrate.

Whitefish Bay Great Pumpkin Festival

The Great Pumpkin Festival at Old Schoolhouse Park in Whitefish Bay stands as one of Milwaukee's longest-running autumn traditions, celebrating over four decades of community pumpkin carving. Running October 22-25, 2025 from 6:00-9:00 PM nightly, this completely free festival provides approximately 1,200 pumpkins from local growers along with all the carving tools, candles, and table space families need to create their jack-o-lantern masterpieces.

What started in the 1970s as a simple lawn display in front of resident Gordy Falk's home has evolved into a major community celebration organized by the all-volunteer Whitefish Bay Civic Foundation since 1986. Visitors pick fresh pumpkins from the patch, carve them in designated tents, then watch as their creations join hundreds of others illuminated on bleachers throughout the park. The festival atmosphere includes live local music each evening, a beer tent, hot cider, food from vendors including Pandl's Whitefish Bay Inn, and a haunted graveyard display by the fountain.

The event welcomes families of all ages to this supervised, community-focused celebration where master carvers create elaborate large pumpkin displays alongside children's first jack-o-lanterns. Located at 5445 N. Marlborough Drive directly across from the Whitefish Bay Public Library, the festival draws thousands of neighbors each night. Some families prefer to take pumpkins home for carving and return them for the nightly display, making this a flexible option for those who want to participate on their own schedule. For questions, contact the Whitefish Bay Civic Foundation at workerbee@wfbcivicfoundation.org.

Bay View's Pumpkin Pavilion

The Bay View Pumpkin Pavilion transforms Humboldt Park into a glowing wonderland of carved pumpkins during its four-day celebration October 15-18, 2025. This free community event brings approximately 10,000 visitors to the park pavilion at 3000 S. Howell Avenue to witness nearly 1,000 illuminated jack-o-lanterns lighting up the night.

The festival follows a two-phase format that invites community participation. On Wednesday and Thursday evenings (October 15-16) from 5:00-10:00 PM, visitors can carve pumpkins that become part of the spectacular display. Then on Friday and Saturday (October 17-18), also 5:00-10:00 PM, the main festivities unfold with all carved pumpkins lit simultaneously during a Grand Lighting ceremony. Created over a decade ago by Bay View resident Bill Rouleau and now organized by the Bay View Neighborhood Association, this entirely volunteer-powered event has become an anchor Halloween celebration for Milwaukee's Bay View neighborhood.

Entertainment fills both evenings with live music from local bands including Dairyland's Finest String Band, Galaxis, The Quilz, and Three Dollar Generals, plus magic shows by renowned magician Tom Burgermeister. Families enjoy face painting, kids' games, food trucks, artistic Halloween installations, interactive performances by First Stage, a community costume parade, and in past years, fire dancing by the Prismatic Flame troupe. Park Road through Humboldt Park closes to vehicle traffic during the event, creating a safe pedestrian environment. The wheelchair-accessible event emphasizes neighborhood togetherness and creative expression, with cleanup on Sunday October 19 from 9:00 AM-12:00 PM when volunteers can take home pumpkins.

For sponsorship or volunteer opportunities, contact the Bay View Neighborhood Association at bvnasponsorships@gmail.com or 414-403-8003.

Hallowings in Greendale offers six days of pumpkin magic

Hallowings 2025 transforms Historic Downtown Greendale Village into a comprehensive pumpkin celebration running October 21-26, 2025 at Gazebo Park. This free event lights up nearly 500 carved pumpkins nightly while offering an impressive array of activities that extend well beyond traditional pumpkin displays.

Families can participate in free pumpkin carving throughout the week, then watch their creations join the illuminated display that glows each evening. The festival grounds feature Pumpkin Bowling and Gourd Golf for active entertainment, while live music fills the park Thursday through Sunday. Spooky kites and spinners add visual interest, and a Giant Pumpkin glows as a centerpiece attraction. The event peaks on Sunday, October 26th with a Halloween Parade at 2:30 PM featuring kids and families in costumes, a Ghostbusters ECTO-1 replica, floats, and a marching band, followed by a costume contest at 3:15 PM. Free candy delights young trick-or-treaters throughout the celebration.

A standout special event, "Pumpkins Over Greendale," takes place Saturday, October 25th at Greendale High School from 11:00 AM-2:00 PM. This spectacle features the Gift of Wings Trebuchet launching pumpkins through the air—with a record flight of 250 feet—in a mesmerizing display of smashing pumpkins. On-site, the Gift of Wings Grill serves brats, hot dogs, burgers, hot chocolate, ice cream, and fresh apple cider mini donuts made on-site.

Festival hours accommodate various schedules: Tuesday-Wednesday 4-8 PM, Thursday 4-8 PM, Friday 4-9 PM, Saturday 11 AM-9 PM, and Sunday 11 AM-8 PM. The event is sponsored by Gift of Wings, Greendale Park and Recreation, and Grand Haven LLC, creating a week-long destination for Milwaukee-area families.

Basse's Happy Jack's Pumpkin Land

For families seeking an all-day pumpkin farm adventure, Basse's Taste of Country / Happy Jack's Pumpkin Land at 3190 County Road Q in Colgate ranks among Wisconsin's largest and most comprehensive operations. Open September 20 - October 31, 2025 (weekdays 1:30-5:30 PM with Tuesday closures; weekends 10:00 AM-5:30 PM), this cashless venue packs more than 65 fall activities into its grounds.

Beyond the pick-your-own pumpkin patch, attractions include an 8-acre corn maze, the Barncade with arcade games, jumping pillow, train rides, duck races, Farmer Skee Ball, barnyard basketball, a ropes course with 17 obstacles, animal barn, giant swing, giant Connect 4, twister mirror maze, tug of war, and wagon rides. The farm continuously expands its offerings and schedules live shows every weekend throughout October: Loop Rawlin's Wildwest Showdown (October 4-5), Lumberjacks (October 18-19), Los Moralitos Stunt Show (October 11-12), Dog Shows (October 25-26), and Pig Races running all October weekends.

Contact 262-628-2626 or visit bassesfarms.com for pricing and additional details about this destination farm.

Buffalo Bill's

Buffalo Bill's Pumpkin Farm at 9612 W Oakwood Road in Franklin operates September 26 - November 2, 2025 on Friday through Sunday from 10:00 AM-5:00 PM. This farm offers over 20 fall activities with free admission to the farm grounds, though individual attractions carry fees. The U-Pick Pumpkin Field runs September 27 - October 27, while families enjoy the giant jump pad and corn pit, pumpkin bowling, pedal kart track, wagon rides, and petting zoo with farm animals.

What sets Buffalo Bill's apart is its Haunted Trail, operating October 3 - November 1 on Friday and Saturday nights. Rated the #1 Top Attraction by Wisconsin Haunted Houses, this after-dark experience provides thrills for older kids and adults, while daytime activities remain family-friendly. New for 2025, the farm has expanded special events throughout the season including Pet Fest, Teacher Appreciation Weekend, and costume contests. Call 414-427-5155 or check buffalobillsfarm.com for current pricing and event schedules.

Jerry Smith's hand-painted pumpkin displays

Celebrating its 50th anniversary in 2025, Jerry Smith Pumpkin Farm at 7150 18th Street in Kenosha has been delighting families since 1975. Open September 13 - November 2, 2025 (Sunday-Thursday 8:00 AM-8:00 PM; Friday-Saturday 8:00 AM-9:00 PM), this iconic destination showcases over 70 hand-painted pumpkin displays that have become beloved traditions for generations of visitors.

Admission runs $9 cash/$10 card on weekdays and $15 cash/$17 card on weekends for ages 3 and up, granting access to the 6-acre Crazy Corn Maze, giant jumping pumpkin pillow, petting zoo, hayrides, kids straw maze, nature trail, face painting, Tire Mountain climbing wall, giant tube play area, and pony and camel rides. The farm's famous frosted sugar cookies and caramel apples add sweet treats to the experience. With extended hours and a comprehensive slate of activities, Jerry Smith's remains a must-visit destination that balances nostalgia with modern entertainment. Contact 262-859-2645 or visit jerrysmithfarm.com.

Budget-friendly pumpkin farms

Several Milwaukee-area farms eliminate admission fees, making autumn adventures accessible for all families. Lindner's Pumpkin Farm at 19075 W. Cleveland Ave. in New Berlin (open daily 10:00 AM-6:00 PM, September 13 - November 2) charges no admission fee and provides free parking, with access to its Big Back Yard costing just $7 weekdays and $9 weekends. The farm features a large pumpkin selection, petting zoo with goats, mini-pigs, llama, mini-horse and bunnies, giant slide, corn maze, Scarecrow Speedway pedal tractor racetrack, and tours of an 1840s log cabin. Individual activities like the Pumpkin Express Barrel Train and Pumpkin Bowling cost just $2 each.

Cedarburg Creek Farm at 649 Highway 60 in Cedarburg (September 18 - October 31; weekdays 1:30-5:30 PM, weekends 10:00 AM-6:00 PM) offers completely free admission with free hay wagon rides. Families pick their own pumpkins while enjoying the barrel train, kid's straw bale maze, corn maze, bouncy houses, pony rides, and a petting zoo ranging from ducks to donkeys. Live entertainment on Saturdays has featured performers like Downtown Harrison and Mr. Pickles. Contact cedarburgcreekfarm.com for 2025 entertainment schedules.

Schuett Farms at W299 S6370 State Road 83 in Mukwonago (September 20 - October 31, daily 10:00 AM-dark) welcomes visitors with free farm admission. Its 12-acre corn maze costs $10 (with a 2025 LEGOS theme), weekend hayrides run $6, and children under 2 enter free. The farm offers pick-your-own pumpkins including giant 600+ pound specimens, a 30-foot slide, corn cannon, pumpkin launching, and hot fresh mini donuts on weekends. Weekend hayride passengers can feed corn treats to Angus cattle during their journey through the farm.

Unique farms features

Some pumpkin destinations combine harvest activities with distinctive attractions. The Elegant Farmer at 1545 Main Street in Mukwonago hosts its Autumn Harvest Fest on weekends September 6 - October 26, 2025 (Saturdays and Sundays 10:00 AM-5:00 PM, with the market open daily 8:00 AM-6:00 PM). Beyond pick-your-own apples and pumpkins, hayrides, pony rides, and a 5-acre family-friendly corn maze, visitors can ride the historic East Troy Electric Train directly to the farm. The experience includes making your own caramel apples and purchasing the farm's famous apple pies in a bag. Free admission with fee-based activities makes this a flexible family destination. Call 262-363-6770 or visit elegantfarmer.com.

Cozy Nook Farm at S11W30780 Summit Ave. in Waukesha operates as a working dairy farm with 65 cows, mostly registered Brown Swiss and Guernseys. Open September 27 - October 31 (daily 9:00 AM-7:30 PM), the farm sells over 40 varieties of pumpkins including orange, white, green Jaharradles, tan New England Cheese, and red Cinderellas, plus gourds, squash, and Indian corn. Weekend hayrides run hourly from 11:00 AM-4:00 PM, and weekday farm tours are available by reservation. Admission costs adults $5 and children under 10 just $3, providing an educational experience about dairy farming alongside pumpkin shopping.

Apple Barn Orchard & Winery at W6384 Sugar Creek Rd. in Elkhorn uniquely combines pumpkin patches and pick-your-own apples with winery tours and tastings at a historic 1865 farmhouse spanning six generations. Every weekend features food trucks and live bands, creating an adult-friendly harvest experience. Check applebarnorchardandwinery.com for fall hours and event schedules.

Specialty attractions

Green Meadows Petting Farm at 33603 High Dr. in East Troy operates October 1-31, 2025 (weekdays and weekends 10:00 AM-4:30 PM, last admission 3:00 PM, closed Mondays and Tuesdays). The $18 credit-card-only admission for ages 2-82 (babies free) includes a free pumpkin from the pumpkin patch during October, plus access to 150+ animals to feed, pig races, rubber duck races, hayrides, combine and firetruck slides, corn crib play silo, large play area, and pony rides for ages 8 and under. Select dates feature a separate Trail of Jack-O-Lanterns event with additional admission.

Creekside Valley Farm at 13101 N. Wauwatosa Road in Mequon (September 20 - October 31, daily 9:00 AM-6:30 PM) provides free farm admission with a corn maze featuring trivia costing $6 (free for ages 3 and under). The pick-your-own pumpkin patch, farm animals, petting zoo, pedal carts, and pumpkin games create an afternoon of entertainment, enhanced by rotating food trucks and live musical performances on weekends.

Barthel Fruit Farm at 12246 N Farmdale Rd. in Mequon (opening September 5, pumpkins available September 18+) features pick-your-own gourds starting in late September and a large variety of unique pumpkins including pink, white, multi-colored, warty, and edible varieties. The on-site bakery truck serves apple cider donuts, streusel muffins, cinnamon scones, mini pumpkin cheesecakes, apple crisp, and cider slush. The farm's Oktoberfest celebration on September 20-21 features Milwaukee Pretzels, beer, and live music, creating an adult-oriented fall event. Free admission makes this an accessible destination.

Haunted attractions and extreme activities

For families with older children seeking more intense experiences, several farms offer haunted trails and spooky attractions alongside traditional pumpkin picking. Swan's Pumpkin Farm at 5930 County Road H in Franksville (weekends in September 10:00 AM-6:00 PM; seven days per week in October) provides both family-friendly activities and scarier options. Free farm admission gives access to pre-picked and pick-your-own pumpkins of all sizes, Corn City featuring celebrity likenesses, a petting zoo, and pedal carts. Activity wristbands cost $14 and include the barrel train, giant slide, pumpkin jump pad, hayrides, and two spooky attractions: Witch Hollow Maze and The Graveyard. This 40+ year family tradition balances gentle and frightening elements.

Meadowbrook Pumpkin Farm & Market at 2970 Mile View Rd. in West Bend (weekdays 12:00 PM-6:00 PM; weekends 10:30 AM-6:00 PM) offers tiered scare levels. The Safari Trail to the animal park (emus, rheas, alpaca, sheep, goats), free weekend wagon rides with pumpkin purchase, and daytime child-friendly Creepy Cornfield provide gentler options. The Night Haunted Cornfield on Saturdays delivers genuine scares for teenagers and adults seeking adrenaline. Free admission with individual activity fees provides flexibility. Visit meadowbrookfun.com for current pricing.

Grappling Gardens at 1800 County Road CC in Richfield showcases 45 varieties of pumpkins in tiny to large sizes, including warty, pink, yellow, blue, white, orange, and flat varieties. Wagon rides transport visitors to the pick-your-own patch, with photo opportunities and pumpkin crafts available. The small family-owned farm hosts special events including Craft Day (September 28), Harvest Fest (October 5), and a unique Pumpkin Throwing Competition & Chili Cook-Off on November 1. Proceeds support local wrestling teams, adding community benefit to your visit.

Community fall festivals a

Beyond large commercial farms, Milwaukee suburbs host neighborhood festivals with pumpkin themes. Greenfield Fall Family Fest at Konkel Park, 5151 W. Layton Ave. takes place Saturday, October 4, 2025 in conjunction with the Annual Trick-or-Trot Run/Walk. This free community event features inflatables, petting zoo, pumpkin bowling, face painting, haystack play area, animal balloons, bingo and games, costume contests with youth and adult prizes, and a pumpkin pie eating contest. The accessible, no-cost format makes this perfect for families exploring multiple October events.

Day Spring Harvest Fest at N14W29489 Silvernail Road in Pewaukee runs October 5 and 12, 2025 with admission of $10 for guests over age 13 and free entry for children 12 and under. Food, bounce houses, hayrides, a treasure trail, and pumpkin patch access create a church-sponsored community gathering with family-friendly atmosphere.

Prospect Hill Garden Center at 19305 W. National Avenue in New Berlin operates pumpkin-focused October weekends (Saturdays 9:00 AM-5:00 PM, Sundays 10:00 AM-5:00 PM). Pick-your-own pumpkins combine with tractor-pulled hayrides through the Ghostly Grove, Krazy Korn Maze, Inflatable Fun Park with cow bouncer, "kiddiepillar," and barnyard bouncer, plus kids games with prizes for $1 each. The Greenhouse Café provides refreshments. This garden center transformation accepts cash, check, debit/credit, and Discover.

Plan your perfect pumpkin adventure

Timing your visit strategically: October weekends bring peak crowds to all pumpkin farms and festivals, with the final two weeks before Halloween experiencing the heaviest traffic. Families seeking shorter lines and more relaxed experiences should visit weekday afternoons when most farms offer reduced admission prices. Early October provides the best pumpkin selection at U-pick patches, while late October delivers the most festival atmosphere at community events with carved pumpkin displays.

Preparing for farm conditions: Wear closed-toe shoes suitable for uneven, potentially muddy terrain, and dress in layers since October Wisconsin weather fluctuates dramatically. Bring wagons or wheelbarrows for transporting pumpkins (most farms provide these, but having your own guarantees availability). Pack hand sanitizer and wet wipes, especially after petting zoo visits and before eating farm treats. Apply sunscreen even on cloudy days, as extended outdoor time causes sunburn.

Maximizing value: Free admission farms like Lindner's, Cedarburg Creek Farm, Schuett Farms, and The Elegant Farmer allow families to enjoy pumpkin selection without entry costs, paying only for activities and pumpkins. Community festivals including the Great Pumpkin Festival, Bay View Pumpkin Pavilion, and Hallowings provide completely free experiences including pumpkin carving supplies. Purchasing activity wristbands at larger operations like Basse's and Buffalo Bill's typically costs less than paying per attraction. Many farms offer weekday discounts and group rates for parties of 10 or more.

Creating memorable experiences: Arrive at carved pumpkin festivals after sunset when illumination creates the most dramatic effect—the Great Pumpkin Festival, Bay View Pumpkin Pavilion, and Hallowings all light displays at dusk. Bring carving tools if festivals permit taking pumpkins home, allowing families to craft designs in comfortable home settings before returning them for display. Pack cameras and phones with charged batteries for photo opportunities at themed displays and with unique pumpkin varieties. Consider visiting multiple farms to experience different atmospheres: community festivals for social experiences, small farms for educational value, and large operations for comprehensive activity sets.

Supporting local agriculture: Most Milwaukee-area pumpkin farms operate as family businesses spanning multiple generations. Purchasing directly from farms ensures money supports local agriculture, and many farms sell additional seasonal produce including apples, gourds, squash, and Indian corn. Farm stands often feature homemade treats like fresh donuts, caramel apples, and pies. Check farm websites and social media pages before visiting, as weather, crop conditions, and special events cause schedule changes. Call ahead to confirm hours and pumpkin availability, especially in late October when supplies diminish at popular locations.

Milwaukee's pumpkin season

Milwaukee's extraordinary collection of pumpkin festivals, farms, and fall celebrations ensures every family discovers their perfect autumn tradition. From the magical sight of thousands of glowing jack-o-lanterns at free community events to all-day farm adventures with corn mazes, animal encounters, and pick-your-own pumpkins, the greater Milwaukee area delivers October experiences that balance nostalgia, education, and pure seasonal fun. Whether you're seeking budget-friendly neighborhood festivals within Milwaukee proper, sprawling agricultural operations in surrounding communities, or unique combinations of pumpkins with wine tasting, historic trains, or working dairy farms, this comprehensive guide points you toward dozens of options throughout September and October 2025.

Start planning your pumpkin tour now by marking calendar dates for time-sensitive community festivals like the Bay View Pumpkin Pavilion (October 15-18), Great Pumpkin Festival (October 22-25), and Hallowings (October 21-26), then fill remaining October weekends with farm visits that match your family's interests and activity preferences. With free admission options, educational working farms, and thrilling haunted attractions all within the metro area, Milwaukee's pumpkin season offers something special for toddlers through grandparents, creating autumn memories that become treasured family traditions.