3 Perfect Days in Bayfield & the Apostle Islands – (tailor-made for first-timers)

Where to Check-In

Lakeside classic – Seagull Bay-A Lakeside Motel – Private balconies right on Lake Superior, trail access, free Wi-Fi, and the best sunrise seats in town.

Victorian charm– Old Rittenhouse Inn (B&B)Gourmet breakfasts & period suites a block from the shops.

Boutique – social hub St. James Social Hotel Art-forward interiors, on-site lounge, easy walk to the pier.

(Rooms fill quickly June-October; book 60-90 days ahead.)

DAY 1 – “Hello, Harbor Town”

Morning/early afternoon – Arrive & drop bags. Stretch your legs on the Brownstone Trail right along side Seagull Bay for lake views and a primer on Bayfield’s sandstone bluffs.

Lunch – Pier Plaza for Lake Superior whitefish baskets or chowder on the patio.

1:15 PM – Board the Apostle Islands Grand Tour Cruise (2.5 – 3 hrs) – lighthouses, sea caves & park lore. Operates daily May 10 – Oct 19.

Late afternoon – Pop into the free Bayfield Maritime Museum for shipwreck stories.

Evening – Sunset cocktails on the Bayfield Inn rooftop, then dinner at the Inn’s waterfront dining room. Reserve if after 6 PM.

DAY 2 – Caves, Culture & Campfire Songs

Breakfast – Wonderstate Coffee – locally roasted; try a Lake Fog latte.

Morning adventure – Guided Sea-Cave Kayak Tour from Meyers Beach (4 hrs). Calm-water alternative: hike the first 2 mi of the Lakeshore Trail for clifftop cave views.

Lunch – Manypenny Bistro – famous for whitefish tacos & Turkish-inspired plates.

Afternoon – Drive the orchard loop: berry-picking at Blue Vista Farm, cider flights at Bayfield Winery, and art browsing at Stone’s Throw Gallery.

Golden hour – Walk the cedar boardwalk at Frog Bay Tribal National Park—the firsttribal national park in the U.S.—to a quiet sand beach sacred to the Red Cliff Ojibwe.

Evening – Shuttle up Ski Hill Rd. for a concert under the canvas at Lake Superior Big Top Chautauqua (think Los Lobos, The Jayhawks, Iron & Wine on different nights). BIG TOP CHAUTAUQUA

Dinner – (pre-show) Legendary Waters Resort & Casino—Ojibwe-inspired entrées and lakefront deck

DAY 3 – Madeline Island & Farewell Flavors

9 AM Ferry – 25-minute ride to La Pointe via the Madeline Island Ferry Line (runs every 30-60 min in summer; weather-dependent). Madeline Island Ferry Line

Morning – Tour the Madeline Island Museum for fur-trade & Ojibwe heritage, then rent bikes/golf carts.

Mid-day – Picnic & swim at Big Bay State Park—the 1-mi boardwalk to the lagoon is a photo favorite.

Lunch – Café Seiche – (farm-to-table) or lakeside at the Beach Club for whitefish sandwiches.

Afternoon – Browse island art studios, grab a scoop at Grampa Tony’s, and catch a mid-afternoon ferry back.

Evening – Last-minute souvenir hunt on Rittenhouse Ave., then splurge on a prix-fixe farewell at Landmark Restaurant in the Old Rittenhouse Inn.

Extra Cultural Touches

Bayfield Heritage Center – rotating exhibits & walking-tour maps.
Red Cliff Fish Company – pick up freshly caught whitefish and watch fishermen at work.
Seasonal events: Bayfield Festival of Arts (Saturday, September 6, 2025, 10:00 a.m. – 5:00 p.m. • Sunday, September 7, 2025, 10:00 a.m. – 4:00 p.m. • Memorial Park) and Apple Festival (1st weekend Oct 3,4,5, 2025) close streets to traffic for music, crafts, and the famed apple-brat.

Practical Tips

Dress in layers – lake breezes can drop temps 10-15 °F by evening.
Book tours & Big Top tickets early (they cap kayak group sizes and sell out holiday weekends).
Parking – free on side streets; metered near the marina May – Oct.
Leave no trace – sensitive sandstone and tribal lands rely on respectful visitors.

Enjoy your first taste of the “Cape Cod of the Midwest.” Questions about reservations or customizing the trip? I’m here to help craft the perfect Bayfield escape. Safe travels!

Swansenreport