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December on a Dime - Week 1: Dec 1-5

Updated: Nov 29, 2022

Welcome to December on a Dime!

Week 1: Dec 1-5, 2022

I am so excited to be your guide to festive events across the state! I love holiday activities, but trying to do everything can add up fast. I hope this helps you plan your weekends and partake in excellent events without breaking the bank. Every featured event will be $25 or less!

Check out our Instagram for a giveaway!

2 winners!

1 winner will receive 2 tickets to Home for the Holidays at Old World Wisconsin on December 10th or 11th.

1 winner will receive 2 tickets to Holidays at Wade House on December 10th or 11th.

Thursday, December 1st

Devil's Head Thursday Night Special - Merrimac, WI - $18 Lift Tickets

Starting at 4pm, lift tickets are ONLY $18. Hit the slopes without breaking the bank! This special goes on every Thursday all ski season long. I recommend packing your own cooler with food and drinks to tailgate in the parking lot. It makes for such a fun night!

Friday, December 2nd

Festive Fridays - Seated Wine & Cocktail Tasting - Wollersheim Winery & Distillery - Prairie du Sac - $25

Casual, seated tastings of some amazing wines as well as a special festive holiday cocktail all paired with some delicious snacks! I love Wollersheim, and it’s so beautiful covered in snow. I highly recommend booking these tickets in advance.

Friday, December 2nd

Christmas in the Ward - Third Ward - Milwaukee - Free/$5 Donation to see Santa

Enjoy all the Christmas spirit in the Third Ward from 5:30 to 8:30pm. There will be live music/entertainment and lots of activities. Come see the tree lighting, tell Santa what’s on your list, and visit with the live reindeer!

All Weekend - December 2nd, 3rd, and 4th

Christmas on the Cranberry Farm - Rooted In Red - Wisconsin Rapids - $15

This is a family experience where you can meet one-on-one with Santa Claus. Enjoy some crafts and Mrs. Claus's milk and cookies while listening to a Christmas story read by Santa himself. We got to experience this cranberry farm this fall and it was amazing! They have warm, cozy cocktails and a wonderful little farm store.

Saturday, December 3rd & Sunday, December 4th

Stroll through a decked out Crossroads Village and hear about festive WI stories and merry memories. I attended this event last year and had such a good time, so I’m so excited to be going back! Old World Wisconsin is remarkable at any time of year, but seeing it covered in snow and decorations really brings out some holiday magic! Last year I got to ride in a horse drawn carriage, get a bunch of new recipes, and learn about Wisconsin traditions. Can’t wait to see what this year has in store!

Saturday, December 3rd & Sunday, December 4th

Santa Express - North Freedom - $25 Adults - $13 Kids

A uniformed conductor will welcome you aboard the train and collect your tickets. Once seated, Santa takes time to visit each and every family during the 55-minute ride. Santa’s elves are also around to help spread Christmas cheer with small gifts for the children.

Saturday, December 3rd

Ugly Sweater Pub Crawl - Wisconsin Dells - $20 in Advance - 21+

Really lean into the holiday spirit with some silly sweaters and drinks! There’ll be holiday swag, games, a vacation package drawing, and exclusive $2 drink specials.

Saturday, December 3rd

Santa Paws - Cudahy - Donation

DOG-FRIENDLY EVENT! Pup photos with Santa and a bake shoppe with dog treats for sale.

Saturday, December 3rd

Jingle & Mingle - Sheboygan - Free/Food Drive

This family-friendly event includes entertainment, a marketplace, a brat fry, trolley rides, and of course, Santa! We plan to visit Sheboygan this holiday season, and I can’t wait!

Saturday, December 3rd

Midnight Magic - Mukwonago - Free

I used to go to this event every year growing up in Mukwonago! Events happen all day, and my favorites are the horse drawn carriage & wagon rides and the fireworks.

Monday, December 5th

Let's Get Lit - Iron Horse Hotel - Milwaukee - Free/Food Drive

I love the Iron Horse Hotel, and they always seem to have fun events going on–this one included! Come hangout and enjoy holiday lights, food vendors, and drinks. This event is free to attend, but you’ll receive 1 drink coupon for every 5 non-perishable food items you donate! All donations are to benefit the Hunger Task Force.


Rotary Lights - La Crosse - Free

DOG-FRIENDLY EVENT! This is one of the best holiday events I have ever been to! There’s a great ice rink with free skate rental, magical carriage rides, and free s'mores by the fire pits to warm your belly. Highly recommended with the family or on a date night. Hayden and I will be heading there for a date night soon!


A holiday experience the whole family can enjoy! Each room is decked out, and no two Christmases are the same. They’ve got it all–from glitz and glam to train tracks and teddy bears around the trees.


Tree of Light - WI Dells - Free

DOG-FRIENDLY EVENT! A towering 55-foot silver maple tree showcases thousands of lights, making it the only light display of its kind in the Midwest. Stroll along the Dells River Walk and view 75 holiday trees while you take in the gorgeous views of the Wisconsin River.

Make sure to tag us @ThatWisconsinCouple on Instagram, Facebook, or TikTok at your festive events! #DecemberOnADime

Huge thank you to the Wisconsin Historical Society for sponsoring this week!


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