12/11/25

Around Town, Neighborhood Spotlights

Sip, Stroll, and Celebrate: A Monroe Street Hot Cocoa Crawl

Winter in Madison is the perfect time to sip something warm, nibble on a sweet treat, and enjoy the city’s festive decorations. If you’re looking for a cozy way to embrace the season, we’ve mapped out a walkable hot cocoa and treat crawl along Monroe Street — complete with decadent chocolates, seasonal drinks, pastries, whimsical holiday fun, a plethora of inflatable Santas and even some holiday shopping along the way!

Stop 1: Madison Chocolate Company

Kick off your adventure at Madison Chocolate Company (729 Glenway Street). Known for its handcrafted chocolate, this spot is a perfect first stop. Start with a warm cup and a small gluten-free treat to pace yourself for the crawl ahead. Don’t forget a photo — your cozy start deserves a snapshot!

Explore their menu before you go.

Walking time to next stop: ~15 minutes along Monroe Street

Stop 2: Infusion Chocolates

Next, stroll to Infusion Chocolates (2503 Monroe Street) for a specialty chocolate experience. Their decadent drinking chocolate is a must-try, and seasonal flavors add a festive twist.

Bonus holiday fun: Keep your eyes peeled along Monroe Street for inflatable holiday Santas! They’re a playful touch and a great spot for a group photo.

Learn more about their process here.

Walking time to next stop: ~3 minutes

Stop 3: Colectivo Coffee

Your third stop is Colectivo Coffee (2530 Monroe Street), a cozy café with seasonal hot chocolate and a warm, inviting atmosphere. Take a little time to sit, enjoy the ambiance, and savor your drink before moving on to the next sweet spot.

Breakfast, bakery, and beverages, they have it all here!

Walking time to next stop: ~3 minutes

Stop 4: Bloom Bake Shop

Just a short stroll away, Bloom Bake Shop (2531 Monroe Street) is your dessert destination. Cookies, pastries, and seasonal treats pair perfectly with hot cocoa — or you can simply enjoy a sweet break before your final stop.

Explore hours, offerings, and locations.

Walking time to next stop: ~5 minutes

Stop 5: Barriques

End your crawl at Barriques (1825 Monroe Street) with a final cup of hot chocolate or a specialty holiday drink. Take your time to enjoy the café vibe and soak in the festive decorations along Monroe Street.

If you’ve had your fill of hot cocoa and treats, Barriques offers a spot to land with food options, wine, beer, and more.

Add to Your Stroll: Holiday Shopping on Monroe Street

Monroe Street is also full of unique shops perfect for holiday gifts. Between your cocoa stops, consider popping into:

• Local boutiques for handmade gifts, jewelry, and seasonal décor
• Specialty stores featuring art, home goods, and one-of-a-kind treasures
• Gift shops with holiday ornaments and festive finds

Mix sipping and shopping for a full afternoon of holiday cheer, local flavor, and cozy fun. Check out all the top Monroe Street Madison shopping spots here.

Whether you’re a local or just visiting Madison, this Monroe Street crawl is a perfect way to combine winter walks, holiday cheer, festive flavors, and local shopping. Grab a friend, bundle up, and let the season’s magic guide your steps — one delicious sip and one perfect gift at a time.