The Perfect Holiday Couples Getaway: 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 just the two of you. The perfect holiday couples getaway. Reimagine your holiday season together.

Escape to Downtown Baraboo for a weekend of thoughtful gifts, cozy coffee stops, shared cocktails, and glowing holiday lights. With two overnights, you’ll have time to explore, unwind, and enjoy the season as a couple.

Day One: Arrive & Feel the Holiday Glow

12 PM: Arrive and start your getaway with lunch at The Relish Tray Bistro & Speakeasy. Try the daily specials and split something special.
1 PM: Browse Angels and Arrows Boutique and Etcetera by BLH for seasonal finds you can pick out together. Continue at Amber Moon and Eye of the Beholder for unique gifts.
3 PM: Take a coffee break at Press Coffeehouse, then grab a pound of coffee to take home.
5 PM: Stroll the Light Up the Square lights display. Book a holiday photo session with Karmen Lindner Photography ahead of your visit for a keepsake of your time together.
6 PM: Grab a burger and an appetizer at Baraboo Burger Company, then play a game together over dinner.
After Dinner: Pick up your Sip the Square passport and share a nightcap at Wiscocktail Lounge.

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

Day Two: Sip, Shop & Unwind Together

9 AM: Start the morning with a coffee date and fresh pastries at Munay Pastry Shop & Cafe.
10 AM: Shop for each other at The Jewelers Edge for a gift with a little sparkle. Then browse A Sense of Adventure and Spirit Lake Trading Company for something you’ll both enjoy.
12 PM: Refuel with lunch at Brothers on Oak. Share a specialty burger and a cold beer, and remember your Sip the Square passport.
1 PM: Explore Countryside ReFind to find pieces for your home together, then stop at Just Crafty LLC for a custom holiday gift and Baraboo Floral & Greenhouse for a festive floral find.
2 PM: Enjoy an afternoon mimosa or spritz for two at Gina Jenny’s. Your Sip the Square passport is almost complete.
3 PM: Treat yourselves to a couples massage at Spa Serenity, booked in advance. Or take a short drive to Balanced Rock Winery for a relaxed wine tasting, with plates to share and live music.
6 PM: Settle in for a cozy dinner at Little Village Cafe. Save room for dessert, and turn your Sip the Square passport at a participating stop before the night is over.

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. Collect your last Sip the Square stamp from Powerline Coffee Co.
10 AM: Browse The Village Booksmith for a cozy winter read to share, then head to Spin Shack for vintage vinyl to play at home.
11 AM: Try something new together at DEZ Tactical Arms, Inc. The indoor range makes a fun date 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: Pick up sweet treats at Sweets on Third to enjoy on the drive home.

Snap a photo of your getaway and share it with us. Tag @downtownbaraboo on social media. #downtownbaraboo

If you want an extra-special weekend, plan your getaway for December 11 or 12 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 to 6 p.m., and Saturday, December 12, 9 a.m. to 4 p.m., with free admission.

Choose Your Home Base for Two

Your holiday getaway starts with the right place to stay. Baraboo, Wisconsin offers lodging options for every style and budget, from romantic cabins to historic bed & breakfasts and modern hotels. Click on a photo below to learn more about each one.