Rails, Sails and Lighthouses
Train rides, boat tours and historic beaconsadd extra dimensions to Wisconsin itineraries
Railroads built Wisconsin’s inland connections, waterways connected it to the world, and lighthouses guided ships safely to shore. Today, Circle Wisconsin members keep that legacy alive, offering planners a wide variety of ways to tap into the state’s transportation history and enjoy scenic views along the way.
On the Water
Lake Geneva Cruise Line’s U.S. Mailboat Tour is a 2 ½-hour cruise that circles southeastern Wisconsin’s beautiful, spring-fed Geneva Lake. Besides narration highlighting the history of the magnificent lakeside mansions and their lavishly landscaped grounds, the tour features the added drama of young mail carriers hopping on and off the moving boat as they deposit letters in pier mailboxes. The only mailboat cruise in the county, passengers cheer on the “mailjumpers,” hoping they make it back onboard without falling into the water (which they sometimes do). The line’s two-hour “Full Lake Tour” does the circuit without the mail stops, and there’s also a cruise that visits 1888 Black Point Estate, a beautiful Victorian home.
The Wisconsin Maritime Museum, located on the Manitowoc River in downtown Manitowoc, is one of the largest such museums in the U.S. Focusing on the Great Lakes and Wisconsin, the museum displays antique boats, ship models, historic shipwrecks, and nautical artifacts, and spotlights Manitowoc’s shipbuilding history as well. One exhibition spotlights the USS Cobia, a restored World War II submarine permanently moored on the river. Walking through the sub, visitors see the torpedo launchers, bunk room, radio room, officers’ quarters, mess hall, and engine room.
The S.S. Badger, another fixture on the Manitowoc waterfront, is a historic car ferry that crosses Lake Michigan twice a day, from mid-May to early October, between Manitowoc and Ludington, Michigan. The last coal-fired steamship still in operation in the U.S., the Badger carries up to 600 passengers and 160 vehicles, including trucks, tour buses, RVs, and farm equipment. During the four-hour, 60-mile crossing, passengers spend their time relaxing on deck, eating and drinking, playing bingo in the main lounge, and watching movies in the theater.
Two Rivers, Manitowoc’s sister community, is also home to Point Beach State Forest. The six-mile stretch of sandy shores along Lake Michigan features Rawley Point Lighthouse, which has been operated by the U.S. Coast Guard since 1853. Another Two Rivers attraction is Rogers Street Fishing Village, a museum complex that comprises a collection of historic buildings on the site of century-old shipping yards on the East Twin River.
The Lake Winnebago Region, boasting one of the largest inland lakes in the country, is a haven for water sports and has acres of beautiful parkland fronting its shorelines. They call it Wisconsin’s Third Great Lake. Fond du Lac’s signature attraction is the lighthouse at Lakeside Park. The region also claims the Horicon Marsh, where visitors can explore the nation’s largest freshwater cattail marsh. Enjoy a scenic view upon the water in a pontoon boat with Horicon Marsh Tours.
In Wisconsin Dells, Dells Boat Tours offers Wisconsin River cruises that pass by majestic sandstone cliffs, gorges, and outcroppings that have been sculpted by wind, water, and time. On the two-hour Upper Dells Boat Tour, passengers disembark to walk through narrow passageways at Witches Gulch and watch a dog leap between towering rock pillars. The one-hour Lower Dells Boat Tour features landmark formations like Hawk’s Bill and Baby Grand Piano.
Also in the Dells, Original Wisconsin Ducks operates rollicking one-hour rides on World War II amphibious vehicles that have wheels and can float. Showcasing secluded canyons and unusual rock formations, the Ducks careen down steep hills and make dramatic plunges into water.
From the Door County village of Sister Bay, Sister Bay Scenic Boat Tours’ 149-passenger Norra Dörr cruises Green Bay, sailing past the bluffs, caves, and lighthouse of Peninsula State Park. On the 90-minute voyage, hear stories of French explorers and early Native American inhabitants. Also popular with groups is the iconic Cana Island Lighthouse, one of Door County Peninsula’s 11 lighthouses. A climb of 97 steps rewards trekkers with sweeping views of Lake Michigan.
Sheboygan, commanding an impressive presence on Lake Michigan, naturally attracts visitors to its lakefront and riverfront. Where the Sheboygan River approaches the lake, original and recreated fishing shanties house coffee shops, restaurants, and boutiques. Charter fishing businesses line the riverfront. Blue Harbor Resort & Conference Center rests on the lake’s sandy shores and has ayear-round waterpark with a lazy river, water slides, and surfing simulator. With big waves on the lake between September and March, Sheboygan is known for its surfing culture and calls itself the Malibu of the Midwest.
Groups also get their fill of maritime heritage at North Point Lighthouse in Milwaukee, Wind Point Lighthouse in Racine, Southport Light Station Museum in Kenosha and 1860 Lighthouse and Light Station Museum in Port Washington, all of which offer panoramas of sparkling blue Lake Michigan.
Up north, the Madeline Island Ferry crosses Lake Superior on a 25-minute voyage between Bayfield and Madeline Island. When motorcoach passengers on the ferry disembark in the town of La Pointe, alocal step-on guide can meet your coach for a tour of the largest and only inhabited island in the 22 Apostle Islands. Groups enjoy shopping in the boutiques and art galleries. The Madeline Island Museum focuses on Ojibwe culture and the island’s past as a French trading post and British settlement.
A must-stop is the Northern Great Lakes Visitor Center in Ashland. Its exhibits provide a look at the Apostle Islands and Lake Superior’s cultural and natural history. Other features include an observation tower, a wildlife viewing platform, a 100-seat theater, and an accessible boardwalk trail.
Legendary Waters Resort & Casino in Red Cliff, on the shores of Lake Superior, makes a good jumping-off point for visits to lighthouses and the Apostle Islands.
Also in northern Wisconsin, St. Croix River Cruises in Hudson offers lunch, brunch, and dinner cruises along the scenic Wisconsin and Minnesota shores of the St. Croix River. Catering is from the kitchen of the Afton House Inn restaurant.
Scenery along the Mississippi River, forming Wisconsin’s western border, enthralls visitors traveling the Great River Road. In La Crosse, breathtaking views of the Mississippi Valley are available from Grandad Bluff, a perfect spot for group photos. Prairie du Chien, a small town at the confluence of the Mississippi and Wisconsin rivers, abounds with historical charm, with attractions like Villa Louis, one of the most authentically furnished Victorian houses in America. Potosi, another Mississippi River town, is home to Potosi Brewery and the National Brewery Museum.
All Aboard for Fun
From the 1916 SOO Line Depot in Osceola, Osceola & St. Croix Valley Railway takes passengers on a 20-mile trip along the sandstone bluffs of the St. Croix River, crossing a bridge into Minnesota, stopping in Marine on St. Croix, and returning to Osceola. Onboard the vintage cars of the diesel-powered train, a host shares stories about the railroad’s colorful history.
More nostalgia is on track at the Railroad Memories Museum in Spooner, a highlight on itineraries in northern Wisconsin’s Washburn County. In the old Chicago & North Western depot, retired railroaders act as tour guides, leading visitors through 13 rooms filled with railroad bells, whistles, lights, tools, timetables, photos, advertising, art, and antiques.
In Green Bay, the National Railroad Museum is one of the largest such museums in the country, showcasing everything from Union Pacific’s legendary “Big Boy” locomotive to General Eisenhower’s WWII command train.
In the Baraboo area, the Mid-Continent Railway Museum in North Freedom offers a seven-mile, 55-minute round-trip train ride on a former branch line of the Chicago & North Western Railway. In a valley between the Baraboo Hills in rural Sauk County, passengers ride in restored steel coaches built a century ago. Besides rides from the 1894 depot, the indoor/outdoor museum displays over 40 train cars and locomotives.
The East Troy Railroad Museum in East Troy keeps history alive with its livingly restored trolleys and interurbans. Groups can step aboard for a scenic 10-mile round trip through rolling countryside and explore exhibits on electric railways of the past.
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Our annual planner will help you craft an unforgettable Upper Midwest group adventure with helpful attraction spotlights, itineraries and listings.

