A chill settles into the woods as Paradise Ranch’s two ebony Percherons effortlessly pull our wagon through a forest gaily lit with thousands of colored lights. Snuggling under a horsehair blanket, I decide this ride is just as delightful sans snow. As we near the barn, a loud, throaty “Ho, ho, HO!” greets us. It feels quite simple, but the experience proves a great way to kick off my visit to Cedarburg, Wisconsin.
Every winter, the city of 11,400 (about 20 miles north of Milwaukee) holds Five Festive Friday Eves between Thanksgiving and Christmas. The celebration features a signature event each weekend at Cedar Creek Settlement, an 1864 woolen-mill-turned-shopping center. This weekend it’s Christmas in the Country and an art fair. Smaller events—ornament making, concerts, the wagon ride I took—flesh out the festivities.
As I unpack in my cozy third-floor bedroom at the Stagecoach Inn, the floorboards creak and groan. The B&B on Washington Avenue, Cedarburg’s main drag, was built in 1853 as a stagecoach inn. I learn a few stories about its history the next morning when owner Brook Brown sits down with me over a steaming mug of coffee. The inn has been a hotel, a restaurant, a tavern, then an ice cream parlor during Prohibition. Today, it stands among six blocks of specialty shops tucked in pretty cream-color limestone buildings backed by the shimmering ribbon of Cedar Creek.
Soon, I’m heading down the street with excited shoppers. I pass an enormous gingerbread house by the community center, then a man selling fragrant popcorn from a wagon. Holly-splashed welcome mats drape over a white picket fence at From the Heart, which specializes in holiday decor. I force myself to pass, intent on getting to the art fair. But I can’t resist Floral Expressions, festooned with snowflake-laden birch trees, poinsettias and velvet ribbons. Pushing through the front door, I stop and ooh out loud. The shop is a riot of greens, reds and golds, with ornaments, swags and collectibles arranged in stunning displays.
Trolleys ring their way through town, carrying shoppers between Cedar Creek Settlement and the booths at the Wisconsin Museum of Quilts and Fiber Arts. At the Settlement, I purchase locally blown glass ornaments for my kids, etched copper earrings for a friend and homemade spice rubs for my mom; at the museum, I snag an enormous ceramic serving bowl decorated with spirals for myself. But the bowl is pretty heavy, and I’m a half-mile from the inn … and there’s a complimentary wine tasting at Cedar Creek Winery. As Cedarburg’s holiday lights twinkle on, I sip wine creekside, surrounded by packages that signal a successful day.
Click ahead for our trip guide on what to do, where to eat and where to stay.
What to do
Cedar Bridge Park Admire Cedar Creek through the lattice trusses of Wisconsin’s only remaining covered bridge. (262) 377-4510
Downtown Dough A haven for bakers, with 2,000 cookie cutters. (262) 387-0311; downtowndough.com 
Five Festive Friday Eves Celebrate the season at these weekend events, including live music, entertainment and complimentary cider. (866) 626-7005; cedarcreeksettlement.com 
Floral Expressions Designer Ron Reel sells beautiful flowers, gifts and more. (262) 377-6361; floralexpressionsbyron.com 
From the Heart A big, yellow house on Main Street sells seasonal crafty gifts and Christmas decor. (262) 376-1016; fromtheheartcedarburg.com 
Marline’s Garden Goodies This garden accessories shop blooms with seasonal decor, whimsical sculptures and art. (262) 375-5050
Paradise Ranch A 30-minute horse-drawn ride (in a wagon or sleigh, depending on snow) takes you past 50,000 colored Christmas lights. (262) 825-7500; paradiseranchwi.com 
Rivoli Theater The Art Deco building has returned to service as a movie house, thanks to the community’s support. (262) 377-1010; rivoliofcedarburg.com 
Weeds Gift Shop Home and garden goods, plus seasonal finds like ornaments and woolen hats, await in this ecofriendly and upcycled shop. (262) 377-0999; lilliesweeds.com 
Wisconsin Museum of Quilts and Fiber Arts In August 2011, an 1850s refurbished barn became the museum’s new home, showcasing an impressive permanent collection and lively traveling exhibits. Admission charged. (262) 546-0300; wiquiltmuseum.com 
Ye Olde Schoolhouse This too-cute quilting store tucks into an 1887 schoolhouse off Cedarburg’s main drag. (262) 377-2770; yeoldeschoolhouse.com 
Where to eat
Amy’s Candy Kitchen Amy’s specializes in candy apples done right. They’re pricey (from $11.99) but big enough to share. (262) 376-0884; amysgourmetapples.com 
Anvil Pub and Grille Tucked into a former blacksmith shop, the eatery offers burgers, steaks and bread with a daily specialty butter. (262) 376-2163; anvilpubandgrille.com 
Cream ’n Crepe Cafe Don’t try to resist the delicious dessert crepes stuffed with ice cream, mousse and berries; you’ll also find soups and sandwiches. Located in Cedar Creek Settlement. (262) 377-0900; creamandcrepecafe.com 
The Farmstead Bar and Grill Locals line up for the steak and signature sides, which include sugar snap peas and garlic mashed potatoes. (262) 375-2655
Java House Warm up with a cup at this friendly coffeehouse, which uses freshly roasted beans and serves specialty drinks. (262) 375-8999
Vintage Cafe and City Deli Refuel on this Tuscan-inspired deli’s soups, salads and paninis, including a great sun-dried tomato. (262) 377-4001; vintagecafecedarburg.com 
Where to stay
The Stagecoach Inn Bed and Breakfast Built in 1853, this B&B maintains a homey feel with friendly innkeepers. Not staying here? Soak in its history in the on-site pub and candy shop. From $100. (888) 375-0208; stagecoach-inn-wi.com 
Washington House Inn The city’s most iconic lodging, the 1886 inn features modern amenities, such as whirlpool baths, and holds a complimentary wine-and-cheese social hour. From $139. (262) 375-3550; washingtonhouseinn.com 
For more information or to plan your trip, contact the Cedarburg Chamber of Commerce. (800) 237-2874; cedarburg.org 
(A version of this story appeared in Midwest Living® November/December 2012.)