May & June - Door County's Summer Festivals Begin!

​Planning Your Door County Getaway — May & June 2026 Festivals
Even though February in Wisconsin still feels like winter, there’s good reason for optimism if you’re dreaming about a spring or early summer escape to Door County with us at Olson Cottages. The coming months are packed with excellent local events, perfect companions to a relaxing stay by the lake.

Jacksonport Maifest
Saturday & Sunday — May 23–24, 2026
While we’re not open for Memorial Day, if you’re in the area, Maifest is a long-running festival that we highly recommend attending.  We’ve even marched in the parade in certain years promoting our cottages to thousands.
This long-running spring favorite celebrates the arrival of warmer weather and community spirit in Jacksonport. Expect a lively juried art fair, family midway and entertainment, classic parade down Hwy. 57, food, music, and even a 10K run and fun walk. It’s a great excuse to make Memorial Day Weekend a memory-making getaway.

Door County Wine Fest
Saturday — June 27, 2026
Sip your way through the peninsula’s celebrated wine trail at the Door County Wine Fest in Baileys Harbor. Held at About Thyme Farm, this event brings together local wineries for tastings, live music, food trucks, and scenic farmland views, perfect for an early summer afternoon.

Door County Beer Festival
Saturday — June 20, 2026
If beer and vibrant summer vibes are more your thing, the Door County Beer Festival celebrates craft brews from around the Midwest in a relaxed farm atmosphere just north of Baileys Harbor. Live music and food pair beautifully with local brews.

Peninsula Art & Craft Events
Door County’s galleries and artisan fairs come alive in May and June with special exhibits and craft markets in towns like Fish Creek and Sturgeon Bay,  perfect for finding one-of-a-kind pieces to take home. (Check local listings as dates are announced closer to the season.)

​Why late May/early June are Great for Your Olson Cottages Stay
Planning ahead is the best way to beat summer crowds while still enjoying robust festival energy. Here’s what you’ll love this time of year:

• Perfect weather: mild days and cool evenings
• Fewer visitors: easier dining reservations and quieter beaches
• Local culture: festivals and outdoor activities in full bloom
• Scenic backdrops: blossoms and green landscapes everywhere

Whether you’re sipping wine in Baileys Harbor, exploring art fairs in Fish Creek, or joining the jubilant Jacksonport Maifest parade, May and June are special in Door County, and ideal for your Olson Cottages getaway.
We currently have availability in our lakefront cottages for the week of May 30th and our Greenwood Cottage is available for the weeks of May 29th, June 6th and June 13th (take all 3 weeks and we’ll give you a nice discount off regular rates!).  As always, you’ll find more info, photos and availability on our website at olsoncottages.com.  We look forward to seeing you this Summer!