Not sure where to begin when planning your trip to Sister Bay? Let our curated seasonal itineraries inspire you! Whether you’re here with family or enjoying a weekend getaway with friends, Sister Bay offers a perfect mix of cozy accommodations, delicious dining, unique shopping, and exciting experiences. No matter the season, there’s always something special waiting for you in Sister Bay.
Cozy Winter Getaways
Winter in Sister Bay offers a peaceful escape with plenty to do for visitors of all ages. As the village slows down, it becomes the perfect spot to relax and soak in the quiet charm of Door County. Start your day with coffee and pastries from Happy Coffee or Zero Sum, then enjoy a hearty breakfast at Al Johnson’s or Cultured Sourdough Bakery.
After fueling up, head out to explore the stunning winter scenery — whether it’s a stroll along the bay or a visit to the Three Springs Nature Preserve. Once you’ve worked up an appetite, cozy up for lunch at Husby’s or Wild Tomato.
For a break from the cold, spend the afternoon bowling at Sister Bay Bowl or, if you’re in the mood for more outdoor fun, head to the Teresa K. Hilander Ice Rink for ice skating or a friendly game of hockey.
Wrap up your day with a delicious dinner at a cozy local spot like CHOP or Thyme Restaurant. Whether you’re here with the whole family or enjoying a weekend getaway with friends, Sister Bay has a variety of charming lodging options to make your stay comfortable. With a perfect blend of relaxation and adventure, Sister Bay is the ideal winter destination.
Refreshing Spring Days
Spring in Sister Bay brings a refreshing burst of life and a beautiful backdrop for a relaxing getaway. Start your day with a coffee and breakfast at Cultured Sourdough Bakery or McEvoy’s Culinaria. Then, head over to Seaquist Orchards to witness the stunning cherry blossoms in full bloom — peaking in mid-May. While you’re there, be sure to visit their farm market to pick up some local treats.
After a morning of natural beauty, take some time to explore the local shops and boutiques throughout the village. For lunch, stop by Dovetail Bar & Grill or SAVOR Barbeque and Taphouse, where you can enjoy delicious, casual fare in a welcoming atmosphere. In the afternoon, unwind with a glass of wine at Twelve Eleven Wine + Provisions while soaking in the spring ambiance.
And to end your day, treat yourself to fresh, flavorful sushi from Fat Belly. Whether you’re visiting for the first time or returning to enjoy the seasonal changes, spring in Sister Bay provides a beautiful setting with plenty to see, taste, and explore.
Lively Summer Adventures
Summer in Sister Bay is the perfect blend of outdoor adventure, relaxation, and charming local experiences. Start your day with a delicious breakfast at Carrol House head over to Al Johnson’s, where you can see their famous goats grazing on the roof.
Spend the morning soaking up the sun at Sister Bay Beach. For a fun way to explore, head over to Sister Bay Boat Rental or Northern Door County Boat Rental or opt for a tour with Sister Bay Scenic Boat Tours or Sail Door County to see the coastline from the water.
In the afternoon, take a leisurely stroll downtown, popping into the local shops and boutiques, and don’t forget to stop by the Country Walk Shops for even more unique finds. For lunch with a beautiful water view, enjoy a meal at Boathouse on the Bay or The Cleat, where fresh local flavors shine.
For a relaxing drink and live music, head to Stabbur Beer Garden or Peach Barn, where you can unwind and enjoy the lively atmosphere. If you’re visiting mid-week, make sure to swing by Waterfront Park for our free summer concert series on Wednesday nights.
Enjoy a memorable dinner at one of Sister Bay’s many upscale dining options, including Waterfront or LURE. End your day with a sweet treat from Door County Ice Cream Factory or indulge in delicious gelato from Door County Creamery. Then, be sure to take in a colorful sunset over the bay. Whether you’re here for a laid-back getaway or an adventurous retreat, there is never a shortage of fun activities to experience during the summer in Sister Bay.
Colorful Autumn Retreats
Fall in Sister Bay is the perfect time to experience the beauty of Door County as the landscape transforms with vibrant autumn colors. Enjoy a cozy lunch from Grasse’s Grill, just a short walk from the waterfront. Another great option is Roots Inn & Kitchen, which offers a cozy pub feel inside and a private back deck raised among the trees.
This season is a fantastic time to explore the peninsula and take in the breathtaking fall foliage. For a unique adventure, try a Segway tour with Segway the Door or Offroad Segway Adventures, or rent a slingshot from Door County Slingshots for an exciting way to cruise around the area. If you’re looking to stay active while on your getaway, check out the Sister Bay Athletic Club, Door County Fitness Studio, or Ironwood Yoga & Pilates Studio for a workout or yoga session.
If you’re visiting in mid-October, don’t miss Fall Fest, a lively celebration with a parade, live music, delicious food and drinks, kid’s activities, and the annual derby race.
