Fall in Milwaukee

Hover or tap a county to raise it; hover or tap a dot for a quick look, then click to jump to the full listing. Arrows on the edge point toward farther day trips. Dot positions are approximate.

The city's marquee downtown Oktoberfest takes over the Summerfest grounds with German food and beer from Kegel's Inn, Leinenkugel's, and Hofbräu München. Beyond the biergarten there are gleefully oddball contests — stein hoisting, brat eating, a Miss Oktoberfest pageant, and a wiener dog beauty pageant.

Henry Maier Festival Park, 200 N Harbor Dr, Milwaukee, WI 53202

Milwaukee's longest-running, most authentic Oktoberfest unfolds in a genuine Bavarian beer garden with the Alte Kameraden band, chicken dances, and steins of Hofbräu. It's spread across several consecutive weekends from early September into early October, so you can pick your date.

Old Heidelberg Park, 700 W Lexington Blvd, Glendale, WI 53217

A lively Waukesha celebration bringing Bavarian music, brats, spanferkel, and wiener schnitzel to Frame Park. Compact and walkable, it's an easy county-seat alternative to the bigger Milwaukee fests.

Frame Park, 1150 Frame Park Dr, Waukesha, WI 53186

Set among restored 19th-century buildings at Dheinsville Historic Park, this 30-plus-year community Oktoberfest pairs German food and beer with genuine historical charm. Admission and parking are free, making it one of the best-value fall outings in the region.

Dheinsville Historic Park, Germantown, WI 53022

One of southeastern Wisconsin's signature fall festivals fills Cedarburg's historic streets with regional wines, craft beer, live music, juried artists, food trucks, and grape stomps at Cedar Creek Winery. The small-town-square setting and pumpkin activities make it a beloved autumn tradition.

Historic Downtown Cedarburg, WI 53012

This open-air historic-farm museum turns the harvest into a hands-on immersion: apple picking, cider pressing, butter and cheese making, and old-world food preservation across five historic farmsteads. You can even clink steins of Oktoberfest ale at the 1930s-style Wittnebel's Tavern. 2026 marks Old World's 50th season.

Old World Wisconsin, W372 S9727 Hwy 67, Eagle, WI 53119

Home of the famous Apple Pie Baked in a Paper Bag, this farm runs weekend harvest fests with pick-your-own apples, an orchard-shaped corn maze, hayrides, pony rides, and East Troy Electric Railroad train rides. Parking and admission are free.

1545 Main St, Mukwonago, WI 53149

A not-so-scary Halloween celebration with a trick-or-treat trail, dazzling light shows, pumpkin animal enrichment, live entertainment, and carving demos. Costumes are encouraged for all ages, and 2026 adds a new daytime Saturday experience.

Milwaukee County Zoo, 10001 W Bluemound Rd, Milwaukee, WI 53226

More than 40 handcrafted illuminated lantern displays — dragons, glowing pagodas, enchanted oceans — line a winding path through Boerner Botanical Gardens after dark. Running nearly two months, it's one of the region's most spectacular fall-evening outings.

Boerner Botanical Gardens, 9400 Boerner Dr, Hales Corners, WI 53130

The Show Dome fills with thousands of chrysanthemums in dozens of varieties, arranged with themed sculptures and seasonal décor under the iconic glass domes. A warm, colorful indoor escape and a 120-plus-year Milwaukee tradition — perfect for a rainy fall afternoon.

The Domes, 524 S Layton Blvd, Milwaukee, WI 53215

A moving Day of the Dead celebration set within Milwaukee's historic garden cemetery, honoring loved ones with ofrendas, music, art, and a run/walk through the arboretum grounds. It blends solemn remembrance with vibrant Mexican-American cultural tradition.

Forest Home Cemetery & Arboretum, 2405 W Forest Home Ave, Milwaukee, WI 53215

Wisconsin's most charming lake village puts its own spin on Oktoberfest with stein hoists, brats, pretzels, polka, and a morning run/walk, capped by live music at historic Siebkens. A scenic day trip that pairs with Kettle Moraine fall color to the south.

Downtown Elkhart Lake, WI 53020

Worked by the same family since the 1800s, Barthel spreads 20-plus apple varieties across gentle North Shore hills, with a pumpkin patch, corn maze, and a bakery turning out cider donuts. Weekends bring brats and a beer garden that make it a hangout, not just a picking farm.

12246 N Farmdale Rd, Mequon, WI 53097

Wisconsin's largest certified-organic apple orchard grows 35-plus varieties across 30,000-plus trees with no synthetic sprays, plus a genuine farm-to-glass hard cider program. The on-site café and bakery turn out warm cider donuts.

5454 County Rd Q, Colgate, WI 53017

A friendly Ozaukee County market where wagon rides ferry families out to the pumpkin patch and the fryer runs cider donuts daily. They grow around 15 apple varieties, including Honeycrisp, for both u-pick and pre-picked buyers.

4177 State Rd 57, Fredonia, WI 53021

With thousands of trees and a wide sweep of varieties, Honey Creek pairs serious apple picking with quirky family fun — think emus and tractor-basketball alongside the cider donuts and pumpkins. A well-loved stop for Cedarburg-area families.

8210 Pioneer Rd, Cedarburg, WI 53012

A tidy Washington County orchard with about 20 varieties ripening in waves and resident bees producing honey sold in the shop. Caramel apples and frozen cider pops make it a sweet, kid-friendly stop.

W220N10550 Amy Belle Rd, Germantown, WI 53022

The big, polished destination of the group shuttles guests to 40-plus apple varieties on a tractor-drawn train and surrounds the orchard with a restaurant, bakery, farm animals, hayrides, and a full family fun park. The most amenity-rich (and busiest) stop.

5006 S Sylvania Ave, Sturtevant, WI 53177

A Racine County favorite with more than 40 apple varieties and a bakery turning out cider donuts, pies, and turnovers. Weekends often add a corn maze and October pumpkin picking — confirm current-year offerings.

25911 Malchine Rd, Waterford, WI 53185

A close-in, family-run orchard first planted in 1948, Awe's keeps things classic with roughly two dozen varieties and a farm stand famous for homemade cider donuts. Being right in Franklin makes it one of the easiest picks for city-side Milwaukeeans.

8081 S Lovers Lane Rd, Franklin, WI 53132

A Walworth County classic that combines the orchard with a working winery, so you can pick apples in the morning and taste house-made fruit wines by afternoon. The country store's pies, cider donuts, and caramel apples round out a full harvest experience near Lake Geneva.

W6384 Sugar Creek Rd, Elkhorn, WI 53121

A National Historic Register orchard growing more than 90 antique apple varieties — some tracing back centuries. You can't pick here, but you can taste apples you'll find almost nowhere else and walk the memorial trail. Apples are sold at the stand on weekend afternoons and at area farmers markets.

19760 W National Ave, New Berlin, WI 53146

A Franksville institution celebrating its 50th pumpkin season in 2026. The yard fills with pumpkins of every size, and an Adventure Wristband bundles a five-acre corn maze, hayride, and kid attractions — while after dark the farm turns to haunted-attraction territory.

5930 County Rd H, Franksville, WI 53126

A high-energy agritourism destination with more than 65 attractions on one farm: an eight-acre corn maze (one of Wisconsin's first), a sunflower maze, giant slides, a ropes course, mirror maze, animal barns, pig races, and a huge pumpkin patch. This is the bells-and-whistles pick.

3190 County Rd Q, Colgate, WI 53017

A Mukwonago favorite whose 12-acre, four-mile corn maze is one of the biggest around and best explored in daylight. Hayrides carry visitors out to pick pumpkins, and the farm stocks all the classic fall décor — cornstalks, straw bales, gourds, and squash.

W299 S6370 State Rd 83, Mukwonago, WI 53149

A Kenosha-area staple since 1975, famous for elaborate hand-painted pumpkin scenes that draw photo-seekers every fall. Kids get pony rides, a petting zoo, bounce pads, and pedal carts alongside the corn maze and hayrides, with apple cider donuts in the country store.

7150 18th St, Kenosha, WI 53144

An authentic, low-key working dairy farm where weekend hayrides roll through the fields before you pick from more than 40 kinds of pumpkins, gourds, and squash. A more traditional, agricultural alternative to the big festival farms.

S11 W30780 Summit Ave, Waukesha, WI 53188

A West Bend farm that doubles as a daytime pumpkin market and, after dark, one of the area's better-known haunted forest and cornfield walks. Daytime hayrides let you pick any pumpkin from the field; the nighttime haunt is a separate, genuinely scary ticketed experience.

2970 Mile View Rd, West Bend, WI 53095

A family farm growing produce since 1890, offering roughly 15 acres of pick-your-own pumpkins. Its twist is the green, leafy “Jungle Maze” — an alternative to the standard dried corn maze — plus late-season sunflower fields and a kids' adventure area.

6521 156th Ave, Bristol, WI 53104

A close-to-Milwaukee New Berlin farm that leans hard into kid-friendly fun: a petting zoo with feeding trails, a 30-foot giant slide, barrel train, pedal-car raceway, merry-go-round, and pumpkin bowling. There's a small per-person admission (a bit more Fri–Sun), and parking is free.

19075 W Cleveland Ave, New Berlin, WI 53146

A Walworth County farm stand with a big variety of pumpkins and gourds plus a corn maze and multiple hay-bale mazes for different ages. Weekend hayrides out to the field are free, and you simply pay for what you pick.

W5740 N Walworth Rd, Walworth, WI 53184

A smaller, low-key Racine County option with u-pick pumpkins sold by the pound, a free corn maze, and an on-site shop with caramel apples. Free entry makes it an easy, budget-friendly stop when the big farms feel like too much.

27225 Church Rd, Burlington, WI 53105

One of the largest and most intense haunts in the Midwest: four connected outdoor attractions across 45 wooded acres at Crystal Ridge, where you flee a clan of mutant cannibal hillbillies down dark trails. Bonfires and a beer tent help you recover afterward, and a daytime not-so-scary party is offered for families.

7900 W Crystal Ridge Dr, Franklin, WI 53132

A heart-pounding walk through 65 acres of dark woods where scare actors ambush you from the shadows. It's a true outdoor experience, so dress for the weather; anyone under 16 must be accompanied by an adult.

9612 W Oakwood Rd, Franklin, WI 53132

The current haunt at the Waukesha County Expo Center — the venue that formerly hosted Wisconsin Fear Grounds (now closed). It follows two twisted twins and their outlaw crew through a cursed farmhouse, leaning on atmosphere, detailed sets, and live actors rather than animatronics.

Waukesha County Expo Center, 1000 Northview Rd, Waukesha, WI 53188

A highly detailed, in-your-face haunt at the Kenosha County Fairgrounds near the Illinois line, with multiple themed attractions for a full night of scares. A destination haunt for the Milwaukee–Chicago border region.

Kenosha County Fairgrounds, 30820 111th St, Wilmot, WI 53192

A 35-to-40-minute journey through a haunted forest that opens into six-plus acres of dense, fog-filled cornfield trails packed with scare actors. Choose your night: daytime visits are genuinely family-friendly, while Friday and Saturday actor nights are the intense ones.

2970 Mile View Rd, West Bend, WI 53095

A guided, candlelit evening walk through the 1892 beer baron's mansion, exploring darkness, loss, hidden compartments, and seldom-seen lower-level spaces. Atmospheric rather than a jump-scare haunt — great for those who like history with their Halloween.

Pabst Mansion, 2000 W Wisconsin Ave, Milwaukee, WI 53233

Ninety-minute guided walks through the “Bloody Third Ward” and downtown, covering old saloons, city scandals, and Milwaukee's most famous haunt — the Pfister Hotel, where staff and visiting ballplayers have reported the ghost of Charles Pfister for a century. Operated since 2008.

Historic Third Ward & Downtown Milwaukee

Wehr's woodland becomes an Enchanted Forest with a cackling witch, a talking owl, and a path lit by 300-plus jack-o'-lanterns — “chuckles and smiles, not nightmares.” The walk ends at the Visitor Center with a snack, live animals, and the nature store.

Wehr Nature Center, 9701 W College Ave, Franklin, WI 53132

Founded in 1974, this is the longest continuously operating haunted house in Wisconsin, with film-quality sets, animatronics, and precise scare actors. Run by the Sheboygan Jaycees, all profits go to local charities — so a visit doubles as a good deed.

2024 N 15th St, Sheboygan, WI 53081

A 138-acre Frederick Law Olmsted bluff-top park stretching a mile above Lake Michigan, with wooded ravines and lake views for easy urban leaf-peeping. In October the ravine canopy lights up above the water — one of the closest quality color spots to downtown.

2975 N Lake Park Rd, Milwaukee, WI 53211

Roughly two miles of ravine trails, lannon-stone staircases, and rustic foot bridges under old-growth beech, sugar maple, and yellow birch — arguably the area's most atmospheric fall hike. You'll cross bridges over a rushing brook with Lake Michigan lapping below.

Grant Park, 100 Hawthorne Ave, South Milwaukee, WI 53172

Six miles of trails wind through 185 acres of forest, ponds, prairie, and Lake Michigan shoreline, and a 60-foot observation tower rises above the canopy for a color view out to the lake. The on-site raptor program adds eagles, hawks, and owls to a fall visit.

1111 E Brown Deer Rd, Bayside, WI 53217

Wisconsin's only urban state forest — 237 acres of woods, grassland, and wetland with six-plus miles of trails inside the city, free to visit. The Purple and Blue trails (with a pond boardwalk) run through hardwood forest that turns color in fall.

6141 N Hopkins St, Milwaukee, WI 53209

Twelve formal gardens sit within an arboretum of maples, oaks, and ornamental trees that glow in autumn, all inside the 660-acre Whitnall Park. Fall is a prime, less-crowded window before the gardens close for the year at the end of October.

9400 Boerner Dr, Hales Corners, WI 53130

A 45-foot tower atop the highest point in Waukesha County looks out over a glaciated forest ablaze in reds and golds, with 20-plus miles of trails from paved paths to challenging grass loops. Climb the tower for the payoff view.

W329 N846 County Rd C, Delafield, WI 53018

The 178-step scenic tower rises 192 feet for one of the most famous fall-color panoramas in Wisconsin — a 360-degree view of hardwood forest glowing across the Kettle Moraine. The wooded approach roads up to the twin-spired basilica are a dramatic fall drive on their own.

1525 Carmel Rd, Hubertus, WI 53033

A 483-acre nature center with miles of boardwalk, paved, and dirt loops through restored prairie and remnant oak savanna that turns russet and gold. The longer Yellow Loop offers the fullest immersion, and prairie grasses add warm autumn tones.

S14 W28167 Madison St, Waukesha, WI 53188

Repeatedly rated one of the best fall-color overlooks in the state, this 60-foot tower on the forest's high ground caps a 3.5-mile loop with a commanding view over woods and farmland in fiery reds, golds, and amber. The Northern Unit also holds 31 miles of the Ice Age Trail.

Parnell Tower Trailhead, County Rd U, Kettle Moraine — Northern Unit

Loop trails roll through hardwood-and-pine moraine terrain, and an observation tower gives an elevated view over Ottawa Lake framed by autumn foliage. The Southern Unit's quieter answer to Parnell Tower.

Scuppernong Trailhead, near Eagle, WI 53119

Home to Wisconsin's last original wooden covered bridge (built 1876), spanning Cedar Creek amid trees that turn brilliant in October, with the color mirrored in the water. A quintessential autumn photo stop just north of Milwaukee.

Covered Bridge Rd, Cedarburg, WI 53012

The largest, most intact wetland in southern Wisconsin, with a boardwalk into the bog and quiet woodland trails for an offbeat fall walk. Tamaracks and surrounding hardwoods lend unusual color to a rare ecosystem.

WI-33 west of Saukville, WI 53080

A glacier-formed lake ringed by 500-foot quartzite bluffs, widely rated among the best fall-color spots in Wisconsin. The East and West Bluff loops (each ~2.5 miles) climb to overlooks where golden and fiery hues spread across the bluffs and reflect in the lake.

S5975 Park Rd, Baraboo, WI 53913

The reconstructed 60-foot Eagle Tower — with an ADA-accessible canopy walkway — puts an observation deck 253 feet above Green Bay over a peaking hardwood forest. Scenic drives like Bayshore Drive string together classic Door County peninsula color.

9462 Shore Rd, Fish Creek, WI 54212

Lakefront's copper-orange Oktoberfest is a Vienna- and Munich-malt Märzen with bread-crust and nutty notes, released each August and pouring through October. The riverside beer hall, pretzels, brats, and legendary Friday fish fry make it the most quintessentially Milwaukee autumn beer stop.

1872 N Commerce St, Milwaukee, WI 53212

Milwaukee's original craft brewery fire-brews a traditional copper Oktoberfest plus a well-known Pumpkin Lager each fall. The family-friendly tour pours samples for adults and unlimited house-made soda for everyone — a rare stop where pumpkin fans and Märzen purists both leave happy.

701 W Glendale Ave, Glendale, WI 53209

Third Space's dark-amber Oktoberfest is a toasty, clean Märzen consistently rated among the city's best fall lagers. The valley taproom runs Saturday tours in season, and the Menomonee Falls location throws a full Oktoberfest bash with yodeling and stein-holding.

1505 W St Paul Ave, Milwaukee, WI 53233

MKE Brewing builds its Oktoberfest from pale, caramel, and toasted Munich malts for a sweet, earthy pour with a bright orange hue. The Bay View taproom on KK Avenue sits in a walkable neighborhood full of fall patios.

2335 S Kinnickinnic Ave, Milwaukee, WI 53207

Widely called the best Wisconsin-brewed Oktoberfest, this 6.25% Märzen is released each fall and sold only within state lines — which makes it feel like a local trophy. Grab six-packs across the Milwaukee area or pair it with a New Glarus day trip.

Available statewide at Milwaukee-area retailers

Since 1946, Five O'Clock has delivered dim lighting, wood paneling, and old-school supper-club warmth that hits perfectly on a cold fall night. The bone-in ribeye is the headliner and the brandy old-fashioned is practically mandatory.

2416 W State St, Milwaukee, WI 53233

Open since 1938, Milwaukee's oldest cocktail lounge has velvet walls, leather booths, and no printed menu — you tell the bartender a mood and they build from 400-plus recipes, ideal for a warm, spiced fall drink. The definition of a cozy autumn nightcap.

1579 S 9th St, Milwaukee, WI 53204

Anodyne's Walker's Point roastery, with Cream City brick and the smell of roasting beans, is a classic autumn refuge, with seasonal pours that lean into fall flavors and frequent live music. For hot cider, the lakefront Colectivo and Stone Creek's Whitefish Bay café are cozy alternatives.

Walker's Point, Milwaukee, WI 53204

Historic downtown Cedarburg hosts its free Wine & Harvest Festival (Sept 19–20, 2026) with a makers market, grape stomps, and food trucks, while the nearby 1876 covered bridge is a postcard fall photo stop. The Shops of Cedar Creek Settlement anchor the weekend in a 19th-century woolen mill.

Cedarburg, WI 53012

Door County peaks with fall color around the third week of October, when the Coastal Byway blazes along the shoreline. Apple orchards and cideries hit their stride, and traditional Scandinavian fish boils run several evenings a week through October, capped with Door County cherry pie.

Door County Peninsula, WI

The 21-mile Geneva Lake Shore Path winds past historic mansions and manicured grounds framed by fall color — a free, walkable way to leaf-peep right at the water's edge. Fall-color boat cruises, farm stands, corn mazes, and zip-lining round out the season.

Lake Geneva, WI 53147

Beyond the waterparks, the Dells sits below the ancient Baraboo Bluffs, best seen on a fall-color boat cruise along the Wisconsin River. Halloween becomes a whole season here with after-dark Ghost Boat tours, haunted houses, and resort trick-or-treating.

Wisconsin Dells, WI 53965

“America's Little Switzerland” charms with Swiss architecture, cheese shops, and its famous namesake brewery. Its Oktoberfest fills downtown each fall with craft beer, live music, wagon rides, and Swiss treats, while the Swiss Historical Village runs autumn cheesemaking demos.

New Glarus, WI 53574

Galena's 19th-century brick Main Street — 125-plus boutiques, galleries, and eateries — sits in the wooded bluffs of the Mississippi River Valley, which reach peak color late September through mid-October. Grant Park offers a classic across-the-river skyline view.

Galena, IL 61036

A 115-mile scenic drive threads oak-maple-aspen forest and glacial hills from Whitewater Lake up to Elkhart Lake, anchored by Holy Hill's basilica and scenic tower. It strings together the best of the region's foliage into one flexible autumn route.

Kettle Moraine State Forest, SE Wisconsin

What are the best fall activities in and around Milwaukee?

The best fall activities in Milwaukee include Oktoberfest celebrations (Milwaukee Oktoberfest downtown, the Bavarian Bierhaus in Glendale), apple picking at orchards like Barthel Fruit Farm and Apple Holler, pumpkin patches and corn mazes such as Swan's and Basse's, haunted houses like The Hill Has Eyes, leaf-peeping at Lapham Peak and Holy Hill, and the China Lights lantern festival at Boerner Botanical Gardens. Family favorites include Boo at the Zoo and Halloween Haunts at Wehr Nature Center.

Where can I go apple picking near Milwaukee?

Top u-pick apple orchards within about an hour of Milwaukee include Barthel Fruit Farm (Mequon), Peck & Bushel — Wisconsin's largest certified-organic orchard (Colgate), Apple Holler (Sturtevant), Awe's Apple Orchard (Franklin, the closest to the city), Jacobson Orchards (Waterford), Honey Creek Orchard (Cedarburg), and Apple Barn Orchard & Winery (Elkhorn). Apple season runs roughly late August through October, and which varieties are ripe changes weekly — call ahead or check the farm's crop line before you go.

What are the best pumpkin patches and corn mazes near Milwaukee?

Standout pumpkin patches and corn mazes include Swan's Pumpkin Farm (Franksville, celebrating its 50th season in 2026), Basse's Taste of Country (Colgate, with 65-plus activities), Schuett Farms (Mukwonago, a 12-acre corn maze), Jerry Smith Farm (Kenosha, famous for painted pumpkins), Lindner's (New Berlin, free admission, great for young kids), and Cozy Nook Farm (Waukesha, a working dairy with weekend hayrides). Most run weekends from late September through October — verify current-year hours and pricing on each farm's site.

When is peak fall color in the Milwaukee area?

In southeastern Wisconsin, fall color typically peaks early-to-mid October, though it varies year to year with temperature and rainfall — some years peak runs into late October. Milwaukee-area day trips like Door County and Baraboo often peak a touch earlier, around the second-to-third week of October. Because timing shifts annually, check the live Travel Wisconsin Fall Color Report or the Wisconsin DNR fall-color guidance before planning a leaf-peeping trip.

What Oktoberfest celebrations happen in and around Milwaukee?

Milwaukee-area Oktoberfests include Milwaukee Oktoberfest on the downtown lakefront (Oct 2–4, 2026), the Bavarian Bierhaus in Glendale (Milwaukee's longest-running, spread across several weekends), Waukesha Oktoberfest (Sept 25–26, 2026), the free Germantown Historical Society Oktoberfest (Sept 26–27, 2026), plus Cedarburg and Elkhart Lake celebrations. Local breweries including Lakefront, Sprecher, and Third Space also release traditional Märzen Oktoberfest lagers each fall.

What are the scariest haunted houses near Milwaukee?

The most intense haunts near Milwaukee are The Hill Has Eyes in Franklin (a huge outdoor screampark), Buffalo Bill's Haunted Trail (Franklin), Desolate Acres at the Waukesha County Expo Center, and Soul Reapers / Terror at the Fair in Wilmot. Note that Wisconsin Fear Grounds has permanently closed. Haunt season runs roughly late September through early November, mostly Friday and Saturday nights — buy timed tickets online, as popular nights sell out.

What family-friendly fall activities are there in Milwaukee?

Family-friendly fall favorites include Boo at the Zoo at the Milwaukee County Zoo, Halloween Haunts at Wehr Nature Center (best for ages 4–10), the China Lights lantern festival at Boerner Botanical Gardens, Halloween Glen from Milwaukee Recreation, the Mitchell Park Domes fall flower show, and the candlelit Illuminating the Dark tour at the Pabst Mansion. Nearly every pumpkin farm — Lindner's, Jerry Smith, and Elegant Farmer especially — is built for kids with hayrides, petting zoos, and mazes.

Where can I see fall colors in Milwaukee without leaving the city?

You don't have to leave the city for great color. Lake Park on the East Side, the Seven Bridges Trail in Grant Park (South Milwaukee), Schlitz Audubon Nature Center in Bayside (with a 60-foot tower), Havenwoods State Forest (Wisconsin's only urban state forest, and free), and Boerner Botanical Gardens in Whitnall Park all deliver vivid autumn foliage close to home. For an easy tower view, Lapham Peak in Delafield is only about 25 minutes west.

What are the best fall day trips from Milwaukee?

The best autumn day trips from Milwaukee are Cedarburg (covered bridge and Wine & Harvest Festival, ~30 minutes), Lake Geneva (the 21-mile Shore Path, ~1 hour), the Kettle Moraine Scenic Drive anchored by Holy Hill, Devil's Lake State Park in Baraboo (bluff hikes, ~2 hours), Door County (fall color and fish boils, best as an overnight), Wisconsin Dells (river color plus Halloween), and New Glarus (Swiss village and Oktoberfest). Galena, Illinois, is a charming out-of-state option about 2.5 hours away.

When does fall festival and harvest season start in Milwaukee?

Fall season in Milwaukee kicks off in September, when Oktoberfests open, apple picking begins, and the Cedarburg Wine & Harvest Festival draws crowds (Sept 19–20, 2026). October is the peak month for pumpkin patches, haunted houses, and fall color, while the season winds down in early November as gardens close and cozy supper-club weather sets in.