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Top Destinations in Wisconsin to Visit This Holiday Season 2021



Wisconsin is the home of Cheeseheads and the Green Bay Packers, and during the holiday season, it’s home to some magical Christmas moments too! Wherever you go in Wisconsin, you’ll find sparkling trees, houses and businesses, and some of the best holiday events. 

If you’re wondering if you can take your fur buddy with you to some of the festivities, the answer is yes. Many furbulous outdoor holly jolly celebrations will welcome pups as long as they’re on leash and well-behaved. So whether you’re headed to Milwaukee, or want to take in some small-town charm, Wisconsin is the place to visit or have a staycation for the holidays.

cat celebrating the holidays

Downtown, Cedarburg

Cedarburg’s beautiful downtown becomes a Christmas wonderland against the backdrop of old limestone buildings and the warm atmosphere of coffee houses and pubs, some of which are pup-friendly. Be sure to ask before venturing inside with Fido. Santa’s gingerbread-style workshop on Washington Avenue and store-front decorations leave no doubt what time of year it is.

  • Kick back with a wine in hand at the dog-friendly Cedar Creek Winery inside the Cedar Creek Settlement shops. During Festive Friday Eves throughout the holiday season, the shops put up lights and decorate their windows, and different events are scheduled each Friday. While your dog can't accompany you in the shops, they can chillax with you at an outdoor table of the winery while you sample the local vintages. Don't furget to bring some dog wine for your thirsty pal! On the way, if you catch Santa and Mrs. Claus wandering the town spreading cheer on Friday and Saturday nights, you may be lucky enough to get a photo with them and your fur-baby.
  • Visit the “Illuminate Ozaukee Drive-thru Holiday Light Show” at Herman A Zeunert Park. For 12 nights, this tour from 5 PM to 8 PM will delight you and the family from the comfort of your car. Sing along with the Christmas tunes on radio station 93.9 FM and vote for your favorite display. You’ll see Santa and Mrs. Claus, the Grinch and Olof from “Frozen.”  While there’s no fee for this furtastic experience, a $10 Goodwill donation will be gratefully accepted. This popular attraction is open from December 13th to 24th.
  • Santa’s Dashaway 5K race takes place on December 11th, starting at 8:30 AM near Santa's Workshop and the Interurban Bridge. The race is open to runners and walkers, including Fido. Holiday costumes, tee-shirts, and race hats will be everywhere. The route is on the dog-friendly Interurban Trail, a paved 30-mile track that leads out of town and into surrounding rural areas. 
  • If you’re aching for some time for relaxation and some exercise for your pup, look no further than Muttland Meadows in nearby Grafton. This 7-acre piece of fenced land is pawfect for mutts eager to lose the leash and break free. The park doesn’t offer clean-up bags and water, so be sure to bring your own.

Downtown, Milwaukee

downtown Milwaukee

Milwaukee is Wisconsin’s largest and busiest city. During the holiday season, its streets abound with light displays and decorated Christmas trees, and its parks are dressed up for the festivities until January 1st.

  • Through the holidays, Cathedral Square Park in the downtown area will be twinkling with 500,000 lights, interactive displays, and animated sculptures all waiting to catch your eye as you stroll around with your fur baby. Over 100 trees await you, all decorated for maximum glow. And don’t miss the Singing Tree!
  • On December 11th, have “Cocoa with the Clauses” in Cathedral Square Park, where Fido is welcome. Open from 11 AM to 2 PM, have your photo taken with the dynamic Christmas duo and enjoy some chocolatey deliciousness. 
  • From now until New Year's Eve, visit Pere Marquette Park on the Milwaukee River for “Hibernation Station,” with its animated bear sculptures, dancing to the sounds of the season on keyboard, horn, guitar, drums, and accordion. Listen on iHeart Radio while you navigate the Jingle Bus audio tour, and be sure to pick up your delightful Jingle Joy Bag filled with edible goodies and a treat for the kids. The park is open daily from 6 AM to 10 PM.
  • At Zeidler Union Square’s, “Home is Where the Hearth Is,” take selfies on the oversized chair there, stand in front of a flickering fireplace, and have your photo taken inside a Seasons Greetings frame.
  • Take a quick detour north to the 3-acre Estabrook Park Dog Park to let your pup run off some excess energy. Open from 5 AM to 10 PM, enjoy all it has to offer with your furvorite pup for $5 a day, or pick up an annual membership for $25 - $30. Or head over to Runway Dog Park, Milwaukee’s largest dog park with 26 fenced acres.

Christmas Village, Chippewa Falls

Chippewa Falls is a historic settlement that offers furbulous outdoor adventure to residents and visitors alike. And during the holidays, it transforms itself into a sparkling village of light.

  • The Christmas Village in Irvine Park is open until New Year’s Day, seven days a week, from 7 AM to 9:30 PM. This event boasts life-sized Christmas scenes that will remind you of the Victorian era, as well as showcasing some local historic replicas. With over 60,000 lights, it’s a sight to behold. Amble with Fido while you finish up your Christmas shopping. This event is free, but donations are gratefully accepted. 
  • Eight hiking trails at the Lake Wissota State Park in Chippewa Falls are open in the winter for cross-country skiing and snowshoeing for leashed and well-behaved pooches and their humans in a winter wonderland. Enjoy the quiet, serene snow scene while you prepare for your next holiday adventure!
  • If you’re longing for some dog-licious food and an adult beverage, hop on over to Every Buddy’s Bar and Grill, where Fido can join you on the outdoor patio for some refreshment. He needs to remain leashed and follow the rules of pet-iquette, but there will be plenty of room under the table for snatching up dropped morsels.

Grand Geneva Lake Resort, Lake Geneva

The Geneva Lake Resort and Spa is a lush, dog-friendly place to visit this holiday season. Pups are welcome, and the resort spoils them with special Grand Geneva bedding and food bowls. This is a pawfect place to stay while you and Fido are sampling all that Lake Geneva has to offer.

  • Lake Geneva Resort holds its Gingerbread House Walk Sundays through Thursdays until Christmas. Drive or stroll past the many creative, decorated cookie houses from 8 AM to PM and vote on your favorite. Local artisans, kids, chefs, and others have worked hard to make the display of gingerbread houses a special holiday experience for all. 
  • On December 18th, bring your kids and your fur baby to a Live Nativity Show at the resort. The show starts at 1 PM and features Joseph, Mary, the baby Jesus, the Three Wise Men, and assorted farm animals and camels. 
  • To satisfy those yearnings to get out on a trail with your pupster this holiday season, White River Park is the pawfect place! With four trails totaling about 4 miles, White River Park is great for snowshoeing and cross-country skiing when the snow falls. Views of the White River and surrounding prairie and grassland make these trails furr-ific!

Downtown, Madison

Madison is Wisconsin's state capitol, and a festive place to be for the holidays. The city's storefronts, homes, and businesses are decorated with lights, trees, and Christmas characters. You may even spy Old St. Nick!

  • Be sure to visit Madison's City Center where you'll find thousands of festive lights and a towering Christmas Tree. Madison's holiday lights will shine all over the city, so drive past some of the more notable sites in your car with your pupper, like the Northern Lights Plaza on State Street, where you'll see large, icy trees and lights. Another furtastic light display is on King Street, and don't miss the Lisa Link Peace Park's market lights that surround a giant Christmas tree.

  • Check out the Madison Night Market on December 16 in the area of the 100 block to the 600 block of State and Gilman Streets. The market will be open 4 PM to 9 PM, and you'll find vendors from all over the city, delicious food from visiting foot carts, and warm drinks. Don't forget to share a morsel of your holiday treat with Fido!

  • For play-minded pet parents and their pooches, River Front Dog Park is a slice of heaven! Fido will love romping with his furry pals while you make merry with the other pet parents on the sidelines. There is an annual pass charge of $10 for locals and $20 for visitors, and day passes are $10. Remember to observe the cardinal rule of dog park etiquette and pick up after your dog. And while there's a water fountain, it's wise to bring your own water, especially in winter when the fountain may be turned off.
  • About half an hour south of Madison is New Glarus, America's Little Switzerland. This Christmas, the Christkindli Market in New Glarus will feature many local vendors, all housed in miniature Alpine chalets with their wares. Stroll the market and find the perfect gift for someone on your list. There'll be food and drink, and plenty of photo ops with Fido. And look for Father Christmas, who will be out and about! The market will be open from December 10th through 12th. Hours are from 4 - 8 PM Friday, 10 AM - 8 PM Saturday, and 10 AM to 6 PM on Sunday. 

Celebrating the holidays about town with your pup is furbulous, but sometimes, events don't welcome pets. If you want to attend an event that doesn’t allow dogs, consider booking an in-home sitter through Wag! to take care of the pup in your home or hotel while you’re out.

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