Madison Holiday Events

Madison Halloween Bar Crawl 2026

Cask & Ale 31 Oct 2026

Madison Halloween Pub Crawl

Cask & Ale 24 Oct 2026

Hall-I/O-ween VI: The Curse of Voodoo Ranger

924 Williamson St, Madison, WI, United States, Wisconsin 53703 31 Oct 2026

Madison Official Thanksgiving Eve Bar Crawl 2026

Downtown Madison 25 Nov 2026

A Christmas Carol at Overture Center - Capitol Theater

Overture Center - Capitol Theater 12 Dec 2026

Wassail! A Holiday Celebration with Aoife O'Donovan & Chris Thile

800 Langdon St, Madison, WI, United States, Wisconsin 53706 10 Dec 2026

Lights on the Lake at The Boathouse

1001 Wisconsin Place, Madison, WI, United States, Wisconsin 53703 28 Nov 2026

Candlelight: Christmas Classics

Monona Terrace - Lecture Hall 11 Dec 2026

12th Annual Holiday Tree Lighting

1001 Wisconsin Place, Madison, WI, United States, Wisconsin 53703 27 Nov 2026

The Dark Holiday Bazaar

3116 Commercial Ave., Madison, WI, United States, Wisconsin 53714 29 Nov 2026

Cash Box Kings

Overture Center for the Arts 27 Nov 2026

Wild Cardz Trio @ One Social Food Hall

One Social Food Hall 23 Oct 2026

Dance Fabulous presents: Ho Ho HO! A Holiday Disco Burlesque Cabaret Spectacular!

The Bur Oak 24 Nov 2026

Run, Santa, Run - 5K

State Street Mall - 825 State Street Madison WI, 53703 12 Dec 2026

Dance Fabulous presents: DiscHo Ho HO! A Holiday Disco Burlesque Cabaret Spectacular!

The Bur Oak 28 Nov 2026

Santa Cycle Rampage- MADISON - Holiday Charity Ride

Breese Stevens Field 12 Dec 2026

Bierock Becomes Paddy's Pub from "It's Always Sunny" for Halloween!

Bierock (2911 N. Sherman Ave., Madison, WI) 31 Oct 2026

The Christmas Bar Crawl - Madison

TBA 12 Dec 2026

2026 Sip and Shop Holiday Art Market

Chazen Museum of Art 3 Dec 2026

PJs & Pancakes with Santa

1001 Wisconsin Place, Madison, WI, United States, Wisconsin 53703 28 Nov 2026

Black Art Expo & Holiday Market 2026

Center for Black Excellence and Culture, Inc. 6 Nov 2026

2026 Edgewater Spalidays

1001 Wisconsin Place, Madison, WI, United States, Wisconsin 53703 2 Dec 2026

Holiday Teas at The Statehouse

1001 Wisconsin Place, Madison, WI, United States, Wisconsin 53703 6 Dec 2026

Harmonious Songwriters’ Showcase: Whitney Mann, Andy Moore, JT Spartz

Harmony Bar & Grill 22 Oct 2026

Hippy Christmas 2026 ft. Pink PHUN Radio

The Bur Oak 19 Dec 2026

Lil’ Badger Consignment’s Holiday Toy Sale

1011 Nichols Road, Monona, WI 7 Nov 2026

A Guaraldi Holiday

800 Langdon St, Madison, WI, United States, Wisconsin 53706 5 Dec 2026

Free Art Friday: Winter Windows

800 Langdon St, Madison, WI, United States, Wisconsin 53706 11 Dec 2026

Breakfast with Santa & Special Guest

1001 Wisconsin Place, Madison, WI, United States, Wisconsin 53703 5 Dec 2026

Cultivate Change Presents Treats Traditions & Togetherness

4710 E Broadway 31 Oct 2026

Joel Paterson – Hi-Fi Christmas Guitar

The Bur Oak 23 Dec 2026

November Activity: Cards for Kids 2026

2701 International Ln, Madison, WI 53704-3125, United States 5 Nov 2026

Energetic Boundaries for the Holiday Season

Madison Death STUDIO + bookshop 12 Nov 2026

Rest & Rebalance: A Post-Thanksgiving Sound Bath

2114 N. Sherman Avenue #6, Madison, WI, United States, Wisconsin 53704 28 Nov 2026

Pictures with Santa

3758 E Washington Ave, Madison, WI 22 Nov 2026

Andy Moore & the Misfit Toys with Chip Cruz

The Bur Oak 18 Dec 2026

Holiday Wreath-Making Workshop

2952 Waubesa Ave, Madison, WI, United States, Wisconsin 53711 1 Dec 2026

Into the Light: A Winter Serenade

Covenant Presbyterian Church, Madison WI 5 Dec 2026

Snowflake Soirée

The Sylvee 2 Dec 2026

Maker's Mark Christmas Party, Liquor Raffle and Ugly Sweater Contest!

2952 Waubesa Ave, Madison, WI, United States, Wisconsin 53711 12 Dec 2026

A Mr. Chair Christmas

Mansion Hill Inn 10 Dec 2026

The Ugly Sweater Party: A Comedy Show

Hotel Indigo Madison Downtown, an IHG Hotel 26 Dec 2026

Calm Before the Holidays: Aromatic Energy, Self-Care, Sound

2114 N. Sherman Avenue #6, Madison, WI, United States, Wisconsin 53704 14 Nov 2026

Holiday Craft Market at La Quadra

72 N Bryan St, Madison, WI 53714-1848, United States 5 Dec 2026

Sparkle & Sip Drag Bingo with Bianca & Kayos: Holiday Hat

The Rusty Bee Lounge 19 Dec 2026

Into the Light: A Winter Serenade

Monona Terrace Community and Convention Center 4 Dec 2026

Breakfast with Santa: The NBA's 21st Pancake Breakfast

3301 Packers Ave, Madison, WI, United States, Wisconsin 53704 5 Dec 2026

Black Feather LLC Holiday Party - Performances, Networking & More!

The Annex at The Red Zone Madison 27 Dec 2026

Waubesa Beach Neighborhood Appreciation Holiday Party

2952 Waubesa Ave, Madison, WI 10 Dec 2026

Diva. Holiday Spectacular Candle Making Workshop

4664 Cottage Grove Rd., Madison, WI, United States, Wisconsin 53716 5 Dec 2026

The Nutcracker Storytime

Fitchburg Public Library 2 Dec 2026

MAHLA Holiday Party

AC Hotel by Marriott Madison Downtown (Madison, WI) 17 Dec 2026

The Nutcracker Storytime

902 Nichols Rd, Monona, WI 53716-2565, United States 16 Nov 2026

From the Garden: Herbal Gift Making

Olbrich Botanical Gardens 5 Dec 2026

Brunch with Santa!

119 King St, Madison, WI 24 Dec 2026

Winter Holiday Dance

500 Kensington Dr, Madison WI 5 Dec 2026

Hoddly Joddly Market

WYSO Center 13 Dec 2026

Fill The Boat for Toys for Tots | SkipperBud's Madison

SkipperBud's 2 Nov 2026

SDM Returns to Bowlavard Lanes

2121 E Springs Dr, Madison, WI 53704-7422, United States 18 Dec 2026

Open Mic/Open Stage: Pre-Samhain/Halloween Chillout Edition

610 North St, Madison, WI, United States, Wisconsin 53704 21 Oct 2026

Lucid Dreaming Sketch Auditions

504 S Brearly St, Madison, WI 53703-3529, United States 28 Oct 2026

2026 Agrace Holiday Pop-Up Shop GRAND OPENING!

141 East Towne Way, 53704 28 Oct 2026

Family Day

6816 Odana Rd, Madison, WI 53719 18 Oct 2026