Twenty-Four Hours in Bayfield


Written in collaboration with Lands’ End, a Wisconsin-based clothing company. Read the published article, Twenty-Four Hours in Bayfield, on the Lands' End Journal. Photography by the talented, Jenna LeRoy Photography.

Nestled on the coast of Lake Superior, Bayfield is one of the Midwest’s best-kept secrets. Originally a village built by lumbermen and railroad barons in the mid-1800’s, Bayfield has evolved to be a thriving community of vibrant artists, sailors, and fishermen that attracts thousands of visitors each year. The unsalted air of the small harbor town (year-round population 475) is filled with nautical vibes and an appreciation for the natural beauty of Lake Superior, the largest of the Great Lakes. Residents and tourists alike sail and paddle on the cerulean blue waters; restaurants bring in fresh fish daily, and local music always seems to be in the air. Bayfield has earned its reputation as “the best little town in the Midwest”. With adventures for every kind of traveler, 24 hours spent wandering Bayfield’s docks and dwellings will peak your interest and have you planning your next getaway.


Day One - arrive + enjoy

In early summer, the brilliant purples of blooming lupines line the two-lane highway to Wisconsin’s northernmost peninsula. Bayfield is a 5.5-hour drive from Madison, WI and a 4-hour drive from Minneapolis, MN.

5:00pm The Bayfield Inn

Upon arrival to the charming town, check in to one of the area’s many accommodations to freshen up and settle in. The Bayfield Inn, located in the heart of town, has a bit of yesterday’s charm with today’s amenities. The Inn offers a variety of rental styles from hotel rooms to vacation homes to accommodate groups of all sizes. Request a lakeside room to wake up to the rhythm of water lapping in Bayfield’s harbor and a million-dollar view of Lake Superior.

6:00pm A Dinner Experience

Treat yourself to a special dinner at Landmark Restaurant in Rittenhouse Inn, known for their 5-course fine dining experience housed in an 1890’s Queen Anne Victorian mansion. After dinner, wander down Rittenhouse Avenue, lined with quaint brick and sandstone buildings, for dessert from The Candy Shoppe – order a scoop of ice cream and their famous wine bread, a Croatian pastry and a local favorite.

Alternatively, eat early and devote the night to music. Catch a concert under the tent at Big Top Chautauqua, hosting both famous musicians and locally grown talent, or enjoy a concert in the park, along the shore of Lake Superior with the harbor’s sailboats as a backdrop for the musical notes.



Day Two - explore the shore

8:00am Caffeine, Lakeside

The perfect day begins with coffee at the newly opened, Kickapoo Coffee Bayfield. Pair their cold fusion, made with local maple syrup, with a freshly baked pastry from Ashland Baking Company. Warm and welcoming, the crisp blue building gives subtle nods to Bayfield’s heritage through the time-worn floor and galley-like cafe.

10:00am Explore Bayfield

For a mid-morning adventure, walk the Brownstone Trail. The 3-mile trail heads south out of town hugging the lakeshore’s brownstone cliffs above the water on an old railway corridor. In the peak of summer, take a short drive out of town to pick a carton of organic, bright red strawberries or fresh blueberries at Blue Vista Farm, with their farm store housed in an old barn. 

1:00pm A Lake Superior Style Lunch

Enjoy lunch at The Bayfield Inn, famous for their Lake Superior whitefish tacos. From the rooftop deck, enjoy the expansive view of Lake Superior with the 21 islands in the Apostle Islands National Lakeshore anchored in the distance. As time slows to a crawl, as it often does in northern towns, watch boats drift in and out of the harbor and the Island Queen ferry return from island time on Madeline Island. 

3:00pm Wander Through Town

Explore the stacks of Apostle Islands Booksellers, known for their impressive collection on Lake Superior and the Apostle Islands. Stroll through the area’s rich maritime history, dating back over 150 years, at Bayfield Maritime Museum. The museum, housed in a stunning boat storage facility, showcases seafaring artifacts and connects visitors with Bayfield’s commercial fishing history and boat building traditions from a bygone era. 

5:00pm Sunset Sail

The lake itself beckons irresistibly, so conclude your 24 hours by raising anchor and setting sail for golden hour on the big lake. Local sailing outfitters, like Manitou Classic Sailing Charters, offer sailing experiences from 1 hour to a full day. Before departing, gather a few local favorites for a picnic on the boat. Buy smoked Lake Superior lake trout from Bodin Fisheries – if the fishing boat just arrived at the dock, take a tour - and beverages from Bayfield Wine and Spirits. With wind in the sails and a glass of wine in hand, watch the sun slip below the horizon to close the first of many adventures to Bayfield.

Getting there