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5 Madison Events to Kick Off the Early Holiday Season

5 Madison Events to Kick Off the Early Holiday Season

As the last of the autumn leaves fall and the air turns crisp, Madison starts to glow with early holiday cheer. November is the perfect time to soak in twinkle lights, shop local, and sip something warm before the December rush begins. Here are five can’t-miss events around Madison, WI to help you celebrate the season early and support local makers, artists, and traditions.

🛍️ 1. Dane County Holiday Farmers’ Market

📅 Dates: Saturdays — November 15 & 22, 2025 (7:30 a.m.–12 p.m.)
📍 Location: Monona Terrace Community & Convention Center, 1 John Nolen Dr, Madison
💻 Info: dcfm.org/markets/holiday-market

Madison’s beloved farmers’ market heads indoors for the winter at Monona Terrace, transforming into a cozy holiday marketplace filled with local food producers, artisan gifts, and festive treats. It’s a one-stop shop for locally sourced jams, baked goods, and handcrafted gifts that’ll make your Thanksgiving table or stocking stuffers extra special.

✨ Tip: Arrive early for the best selection — and take a stroll along Lake Monona afterward for classic Madison winter views.

🎨 2. Art & Craft Fair at VFW Post 7591

📅 Date: Saturday, November 29, 2025 (9 a.m.–3 p.m.)
📍 Location: 301 Cottage Grove Rd, Madison, WI 53716
💻 Info: isthmus.com/events/art-and-craft-fair-vfw

This cozy post-Thanksgiving fair is the perfect excuse to shop small while avoiding big-box chaos. You’ll find handmade jewelry, woodcrafts, art prints, and more from local artisans. Free admission and an easygoing atmosphere make it ideal for casual holiday shopping.

✨ Pair it with brunch nearby at Daisy Café or Crema for a full Saturday outing.

🎁 3. Holiday Craft Vendor Fair at the East Side Club

📅 Date: Saturday, November 15, 2025
📍 Location: The East Side Club, 3735 Monona Dr, Monona
💻 Info: Event Listing (Facebook)

Enjoy lakefront views while shopping from dozens of local vendors offering ornaments, home décor, jewelry, and baked goods. This event combines holiday shopping with a scenic backdrop and community feel — a must for east-siders.

✨ Tip: Stay for lunch or a drink at the East Side Club’s bar overlooking Lake Monona.

✨ 4. Shine On Madison – Downtown Holiday Light Ceremony

📅 Date: Sunday, November 23, 2025 (approx. 4 p.m. – 8 p.m.)
📍 Location: Lisa Link Peace Park & State Street / Capitol Square
💻 Info: visitmadison.com

Nothing says “holiday season” like downtown Madison lighting up for the first time. Shine On Madison features the official light ceremony, live music, family activities, and festive treats. It’s a great kickoff event that sets the tone for the city’s holiday season.

✨ Tip: Bundle up, grab a hot cocoa from Michelangelo’s or Ancora, and stroll State Street to see the lights reflect off the Capitol dome.

🧶 5. Madison Makers Black Friday Market & Pub Crawl

📅 Date: Friday, November 29, 2025
📍 Location: Multiple venues (Hotel Indigo, The Deliciouser, State Line Distillery & more)
💻 Info: isthmus.com/arts/madison-holiday-arts-crafts-fairs-markets-2024

Skip the mall lines and support small makers instead! The Madison Makers Market hosts a Black Friday edition across several downtown venues, pairing local crafts with beer, cocktails, and community vibes. It’s a laid-back, distinctly Madison way to do your holiday shopping.

✨ Tip: Go with friends and turn it into a mini walking tour — you’ll find everything from handmade candles to quirky prints and winter wear.

Madison shines in November, blending cozy community events with the sparkle of early holiday excitement. Whether you’re chasing lights, sipping cider, or getting your holiday list started, these events offer the best way to celebrate local and stay merry!

-By Andie White

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