Celebrate the holiday season with a day of shopping, music, and small-town charm during Shop, Sip & Stroll in historic downtown Madison on November 15 & 22, 2025, from 10 a.m. to 5 p.m.

Guests can enjoy exclusive deals and discounts from participating retailers while sipping on complimentary festive beverages and exploring Madison’s beautifully decorated downtown. Live music will fill the streets, adding to the warm, Hallmark-worthy atmosphere that makes this event a local favorite.

Start your day at the Host Tent, located beside the Welcome Center at 115 E. Jefferson Street, to pick up maps, event information, and special giveaways (while supplies last). Then stroll, shop, and savor the joy of the season at your own pace.