Hire a car Monday morning and head northwest on Interstate 94. The Wisconsin border is 90 minutes away; the lake country begins before that. October in Wisconsin and Milwaukee: This is peak fall foliage season in the upper Midwest. The maples and oaks of Lake Geneva and the Milwaukee River valley are in full colour in mid-October - the specific combination of sugar maple red, oak bronze, and birch yellow that makes the Great Lakes region one of the more compelling autumn colour destinations in North America.
Nights One and Two: Lake Geneva
Lake Geneva is a resort town of 8,000 on the western shore of Geneva Lake - a glacial lake formed by the last ice age's retreating lobes, surrounded by the estates and mansions built by Chicago's wealthy families from the 1870s onward when the railway made the 90-mile journey practical for weekend retreats.
The Geneva Lake Shore Path is the specific post-marathon asset: a continuous 32-kilometre path running around the entire perimeter of the lake, passing directly in front of every estate and mansion on the shoreline. The path is legally required to remain public because Wisconsin water law mandates public access to navigable waterways; the estates cannot fence their lake frontage. The section immediately south and north of the town centre is flat, paved, and passes through the concentrated estate district. In October, the private grounds behind the mansions are in full fall colour above the lake path.
Where to stay: The Grand Geneva Resort is the full-service lake resort option - indoor pool, ground-floor accessible rooms, and direct access to the shore path.
Nights Three and Four: Milwaukee
Drive 45 minutes north on Route 43 to Milwaukee - Wisconsin's largest city, population 570,000, built at the confluence of three rivers where they meet Lake Michigan.
The Milwaukee RiverWalk is a continuous flat path running 4.8 kilometres along both banks of the Milwaukee River through the Historic Third Ward, downtown, and the Beerline neighbourhood - a timber and stone boardwalk at river level, lined with restaurants, galleries, and the former industrial buildings that Milwaukee's 19th-century brewing economy produced. October on the RiverWalk: the maples along the riverbanks are in full colour, the outdoor terrace seating has been brought indoors, and the river runs dark and fast after the autumn rains.
The Milwaukee Art Museum (MAM, entry approximately $25) on the lakefront is a Santiago Calatrava building from 2001 - the Quadracci Pavilion, with its moveable steel brise-soleil that opens and closes like wings twice daily. The collection covers American art from the 18th century to the present, with particular strength in German Expressionism. The interior is entirely flat at each level.
Where to stay: The Kimpton Journeyman Hotel in the Third Ward (directly on the RiverWalk) is the most appropriately positioned option.
Where to eat: Odd Duck on Florida Street is the current Milwaukee fine-dining reference - local and regional sourcing, seasonal menu, small plates. For the specifically Milwaukee experience: Kopp's Frozen Custard serves a different flavour of the day each day from multiple Milwaukee locations, as it has since 1950.
Getting Home
Interstate 94 south from Milwaukee to Chicago O'Hare International Airport (ORD) takes approximately 75 minutes in normal traffic.