Middleton Winter Happenings

Whether enjoying a cup of hot chocolate or a snowflake-shaped sugar cookie, admiring twinkling lights or meeting up at a local event, the holidays are about spending time with loved ones. There’s so much going on in Middleton, you’re sure to be filled with joy. Let us help brighten your holiday spirit with this guide to the holiday season in Middleton.

Warm up with a drink

It’s simply not the holiday season without a peppermint mocha or a steaming cup of hot chocolate. No matter what you like filling your mug with, multiple spots in Middleton sell seasonal beverages that’ll make your taste buds pop and warm you up.  Check out Grace Coffee Co. downtown and its seasonal drinks, including gingerbread-flavored cold brew, lattes and chai tea, as well as Barriques Coffee Roasters, where you’ll find yourself an eggnog, gingerbread or peppermint latte. When on the northeast side of town, stop into Prairie Café & Bakery to order a seasonal hot drink and a warm breakfast. Swing by the drive-thru at Starbucks, MOKA or Scooters Coffee for various holiday-themed drink options.  

Treat Yourself to a Holiday Goodie

Who can say “No” to a sweet treat? Exploring Middleton’s bakeries is a fun outing for the whole family. Check out a variety of delicious, made-from-scratch loaves of bread, cakes, pastries, confections and more at Middleton’s longest-standing bakery, Clasen’s European Bakery. Each year, Clasen’s goes into full winter holiday mode, with seasonal treats galore and, most notably, a child-size gingerbread house in the back of the shop.

A stop at Miggy’s Bakes puts a smile on anyone’s face. This pretty, pink bakery has a dessert case filled with unique-flavored cookies, cookie cups, cakes, brownies and bars. During the holidays, you’ll find the cutest winter-themed cut-out sugar cookies. Plus, on Saturdays and Sundays, the bakery serves fresh cinnamon rolls.

Longtable Beer Cafe has added a holiday “dessert board” which includes eggnog, peppermint chocolate cake, and cookies.

And do not forget Hubbard Avenue Diner’s bakery counter filled with pies, cakes, cookies, brownies and seasonally decorated sugar cookies. Hubbard also carries Chocolate Shoppe Ice Cream, perfect for a sundae or milkshake.

Delight in Downtown’s Winter Window Stroll

Stroll through downtown Middleton and see windows decorated with adorable, hand-painted gnome winter scenes. Local artist Anne Bamberg intricately hand-painted festive gnomes on 14 windows across downtown Middleton with sweet nods to the stores they adorn — for example, the gnomes are decorating a tree at The National Mustard Museum using pretzels and mustard! You’ll be amazed by the beauty of these charming window paintings.

Enjoy Capital Brewery’s Keg Tree

Stacked 18 feet high with 287 half-barrels, Capital Brewery and Bier Garten’s “keg tree” is a sight to see. Admire this tree while enjoying one of their award-winning beers inside the cozy Bier Stube. This brewery has been around since 1986, brewing German-style lager, and now also offering a variety of American-style ales, barrel-aged beers and IPAs.

Find the Unexpected at The National Mustard Museum

This is a fun place to bring visiting family for an afternoon. The museum is free and full of memorabilia and more than 6,700 jars and tubes of mustard to look at. The shop upstairs contains more than 200 kinds of mustard for sale and other delicious food items, like barbeque sauce, chocolate toppings, jams, maple syrup and more, as well as hilarious gift items and Wisconsin-themed gifts.

Join the Fun at These Middleton Events

• Hidden Cave Cidery Drag Brunch: On Dec. 16, Mr.Gay Wisconsin, Michael Lynn, will host a drag brunch at Hidden Cave Cidery. There will be performances by three dancers and a full breakfast buffet featuring food from Vessel Café. The doors open at 10 a.m., brunch will be served at 10:30 a.m., and the show will begin at 11:15 a.m.
• Gingerbread House Workshop: Children aged 5 and older are invited to celebrate the holidays with a crafting workshop from 2-4 p.m., Dec. 17, at Rock Paper Scissors. Children will decorate paper gingerbread houses and ornaments.
• Middleton Community Orchestra Holiday Concert: Enjoy Middleton Community Orchestra’s Holiday Concert at Hamel Music Center. The concert begins at 7:30 p.m. on Dec. 20 and will feature two soloists, Lindsay Flowers on oboe and David Perry on violin. Tickets can be purchased at Willy Street Co-op West and at the door on the night of the show.  
• Make Music Winter: Celebrate the shortest day of the year, Dec. 21, with music in Stone Horse Green and a parade around downtown Middleton. The parade will begin at 3 p.m. All are welcome to join the parade to play instruments and sing carols.
• Fleet Feet New Year’s Day Dash: The 19th Annual Fleet Feet New Year’s Day Dash will begin at 10 a.m., Jan. 1, 2024, at KEVA Sports Center in Middleton. This event is a 5-mile chip-timed run and a 2-mile walk, followed by a party, great prizes, complementary beverage tokens, and giveaways.