Stay: For a spot down on the riverfront where the action is, check availability at Harbor Winds Hotel, within walking distance of Sheboygan’s downtown, or Dumper Dan’s Condominiums, right next to the charter fishing fleet. If you prefer to stay on the edge of town, check out the Holiday Inn Express with complimentary continental breakfast served every morning.
Eat: For a casual atmosphere, drinks and award-winning wings, head downtown to Legend Larry’s. Whatever temperature, whichever flavor you crave, Larry’s will leave you satisfied.
Race: More than just a day at the races, Road America in Elkhart Lake offers a wide range of opportunities for groups of all sizes. Plan to be around during NASCAR, the MotoAmerica SuperBike Doubleheader, Vintage Car Weekend or any of the other amazing events they host.
Cheers: The 8th Street Ale Haus is your home for great beer in Sheboygan. With 30 draft lines and over 70 bottled beers, there is something for every taste. Pair your favorite beer with your favorite gastro-pub meal.
Golf: Bring your golf clubs and enjoy an early round of 18 holes. Sheboygan County boasts some of the best golf courses in the state and is one of the top golf destinations in the world, with Whistling Straights, host of the 2004, 2010 and 2015 PGA Championships, and the 2020 Ryder Cup, and Blackwolf Run, host of the 1998 and 2012 United States Women’s Open. You’ll also find The Bull at Pinehurst Farmswhich is the only Jack Nicklaus Signature Gold Course in the state. The area is also home to courses for golfers of all levels including traditional gems such as Riverdale Country Club and Quit Qui Oc Golf Course.
Dine: After a day on the green, stop at The Horse & Plow in Kohler for some grub. This casual historic tavern was once the taproom for Kohler Co. workers who lived at The American Club.
Unwind: Enjoy cigars from some of the most distinguished cigar manufacturers in the world, complemented by your favorite scotch, cognac, wine or martini in Olive N’ Ash’s comfortable, living room-like atmosphere.
Explore: Did you know that Sheboygan is the Fresh Water Surf Capital of the World! Head downtown and check out EOS, Wisconsin’s only surf shop. Rent a kayak, stand up paddle board or try surfing!
Fish: Don’t forget to book a charter fishing excursion while you’re here! Sheboygan offers some of the best trout and salmon fishing on Lake Michigan, with some of the best charter fleets in the state. Then, whatever you catch, be sure to take it to Schwarz Fish Market to have it smoked, processed and shipped home.
Snack: After a long day on the lake, stroll down South Pier and stop at Angler’s Avenue Pub & Grill and Angler’s Avenue Pro Shop. Angler’s Pro Shop is Lake Michigan’s friendliest tackle store. The Grill offers a full menu of great homemade foods that are sure to please your appetite. Friday nights are the hottest night with their famous fish fry.