The Perfect Holiday Girls’ Trip: Downtown Baraboo, WI

Name: Downtown Baraboo
Address: P.O. Box 216, Baraboo, WI, 53913
Telephone: 608.448.3490
Location: Downtown Baraboo

Discover the Spirit of Christmas in Downtown Baraboo, Wisconsin
Plan an overnight getaway for you and your friends. Create the perfect holiday girls’ trip.

Escape to Downtown Baraboo for a weekend of thoughtful gifts, cozy coffee stops, delicious meals, and holiday lights. With two overnights, you’ll have time to explore, unwind, and enjoy the season together.

Day One: Arrive & Discover Your Christmas Spirit

12 PM: Arrive and start your holiday girls’ trip with lunch at The Relish Tray Bistro & Speakeasy. Enjoy their daily specials.
1 PM: Explore Angels and Arrows Boutique, Johnny’s Girl Boutique, and Etcetera by BLH for seasonal trends and accessories. Continue browsing at Amber Moon and Eye of the Beholder for the perfect unique gifts.
3 PM: Take a coffee break at Press Coffeehouse, grab a pound of coffee to take home, then stop at Corner Drug Hometown Pharmacy for a unique holiday ornament.
5 PM: Stroll the Light Up the Square lights display. Arrange a holiday photo session with Karmen Lindner Photography ahead of your visit for a special keepsake with your girlfriends or partner.
6 PM: Grab a burger or apps and a game at Baraboo Burger Company.
After Dinner: Grab your Sip the Square punch card and enjoy an after-dinner drink at Wiscocktail Lounge.

Light installations by the Baraboo Sauk County Courthouse. A Christmas tree, ornament and arches, all made with Christmas Lights.

Day Two: Shop, Sip & Reclaim Your Calm

9 AM: Start the morning with a coffee date and delicious pastries at Munay Pastry Shop & Cafe.
10 AM: Browse Bekah Kate’s for the chef on your list, A Sense of Adventure for the explorer, and Spirit Lake Trading Company for the nature lover. Then visit The Jewelers Edge for a gift with a little sparkle.
12 PM: Refuel with lunch at Brothers on Oak. Choose a specialty burger and a tap of cold beer. Remember your Sip the Square card.
1 PM: Explore Countryside ReFind to deck out your home, Recycled Sally’s for the perfect holiday party outfit, and Just Crafty LLC for a custom holiday gift. Stop at Ardyth’s Sew-n-Vac Shoppe for the sewing enthusiast on your list and Baraboo Floral & Greenhouse for a festive floral find.
2 PM: Grab an afternoon mimosa or spritz at Gina Jenny’s. Your Sip the Square is almost complete.
3 PM: Reclaim your calm with a facial or massage at Spa Serenity, booked in advance. Or take a short drive to Balanced Rock Winery for a relaxed wine-tasting break, with delicious plates to share and live music. Soak in every wonderful moment of this holiday girls’ trip.
6 PM: Settle in for a cozy, delicious dinner at Little Village Cafe. Don’t forget dessert. Turn your Sip the Square card at one of the participating stops and enter to win a trip back to Downtown Baraboo.

Three women shopping in a store for Christmas decorations. Looking at a large glittery white ornament and smiling.

Day Three: Linger a Little Longer

9 AM: Ease into Sunday with coffee and a light breakfast at Powerline Coffee Co or Coffee Bean Connection. Grab your Sip the Square punches.
10 AM: Pick up the perfect unique gifts for the little ones at Just Imagine Toys, then stop by Neat-O’s Bake Shoppe for holiday cookies to take home. Browse The Village Booksmith for your next cozy winter read, then explore Spin Shack for some vintage vinyl.
11 AM: Make time for DEZ Tactical Arms, Inc. Work off some energy at the indoor range before you hit the road.
12 PM: Enjoy one final meal at Little Village Cafe, Baraboo Burger Company, or Brothers on Oak. Pick your favorite.
1 PM: Grab some sweet treats for your stockings at Sweets on Third. Swing back to your favorite store to grab those last-minute gifts.
Snap a photo of your crew in downtown and share your experience with your friends. Tag @downtownbaraboo on social media. #downtownbaraboo

If you want an extra-special weekend, plan your getaway for the weekend of December 11 to attend the Very Merry Holiday Fair! Browse artisan gifts and handmade treasures at the Baraboo Arts Building, 323 Water Street, Baraboo, WI. The 2026 fair takes place Friday, December 11, noon–6 p.m., and Saturday, December 12, 9 a.m.–4 p.m., with free admission.

Choose a Great Lodging Accommodation for your Holiday Girls’ Trip

Your holiday getaway starts with finding the right place to stay. Baraboo offers a variety of lodging options for every style and budget. Click on a photo below to learn more about each lodging option. Baraboo has everything from cabins to historic bed & breakfasts to modern hotel facilities.