Base: Saugatuck or Douglas, both nights. The drive from Chicago is about 140 miles on I-94 and I-196, less than two and a half hours without traffic, and Michigan runs an hour ahead on Eastern time. Walking Water Street and the riverfront is free. Pace: easy: the drive, then about 2 miles on foot between the two villages’ downtowns, with the break at a long lunch.
The drive around the lake
Leave the city early, before the Friday traffic builds on the Dan Ryan and the Skyway, and the drive around the bottom of Lake Michigan is easy: I-94 through northwest Indiana, then I-196 north along the Michigan shore. Somewhere past the state line the billboards give way to orchards and vineyards, and someone in the back seat starts the playlist over. Set your watches forward an hour at the Michigan line. You will roll into Saugatuck in time for a late breakfast if you leave by 7 a.m. Chicago time.
Coffee on Hoffman Street
Where to eat: Uncommon Coffee Roasters, at 127 Hoffman Street in downtown Saugatuck, open from 7 a.m. daily, for coffee and a pastry after the drive.
First stop, before anyone checks in: coffee. The roaster’s cafe sits a block off the river, and on a summer morning the tables outside fill with people in beach clothes planning their day. Take your cups down to the water and stretch your legs along the boardwalk while the boats idle out toward the lake.
A brewery lunch in Douglas
Where to eat: Saugatuck Brewing Company, which has taprooms in both villages, for a long lunch of pretzels, burgers and fries on the patio at its Douglas pub.
Settle the plan before the first round, which is the honest part of a brewery lunch: pick a designated driver for the day, and keep the rest of the afternoon on foot. The brewery makes its beer here in Douglas, and the patio is a warm, loud, easy place for the group to catch up on everything that happened since the last trip. Order a second board of pretzels. Nobody is in a hurry.
Water Street and an early drink
Back in Saugatuck, the afternoon is for wandering: galleries, a bookshop or two, boutiques in white clapboard storefronts and ice cream counters along Water Street and Butler Street, with the river and the boats on one side. Douglas, just across the bridge, has its own quieter Center Street with shops and a few cafes. Late in the afternoon, stop at Borrowed Time on Center Street in Douglas, open from 4 p.m. on Fridays, for a drink or something from its wine window before dinner. Expert tip: park once for the afternoon and walk between the two downtowns; it is about a mile and a half on the bridge over the Kalamazoo, and summer parking near Water Street fills by midday.
Dinner on the river
Where to eat: The Butler, on the waterfront in downtown Saugatuck for more than 60 years, for the Butler Burger or seafood with a view of the river.
Ask for a table by the windows or out on the deck, where the boats slide past in the evening light. Then walk the riverfront after dinner, when the town quiets down and the docks glow under the lamps.
Where to eat and stop
- Breakfast · Uncommon Coffee Roasters — 127 Hoffman Street, from 7 a.m. daily. Why here: Coffee and a pastry a block off the river right after the drive from Chicago.
- Lunch · Saugatuck Brewing Company — taprooms in Saugatuck and Douglas; check its hours. Why here: A long brewery lunch on the patio in Douglas, with a designated driver picked first.
- Dinner · The Butler — on the waterfront downtown for more than 60 years; book ahead for a group. Why here: Dinner on the river on the first night, with burgers, seafood and the boats going by.
- Quick stop (other): Borrowed Time — 22 E. Center Street, Douglas; from 4 p.m. Wednesday to Friday, from 2 p.m. at weekends. Why here: An early drink or a glass from the wine window on Center Street before dinner.
Chicago → Saugatuck: about 140 miles on I-94 and I-196, roughly 2.5 hours. Downtown Saugatuck → Douglas: about 1.5 miles, roughly 30 minutes on foot or 5 minutes by car.
Where to stay
- A cottage, inn or rental in Saugatuck or Douglas — two nights in one place, close enough to walk to Water Street and dinner.
Dinner: The Butler, on the river in Saugatuck.
Tomorrow: the 303 steps up Mt. Baldhead, Oval Beach and pie in Fennville.
Bad-weather plan
Rain on the drive over? Lean into the brewery lunch and the shops on Water Street and Center Street, which are made for a wet afternoon, and save the river walk for after dinner when storms over the lake often clear.
Stay: Saugatuck base · Anchor: Water Street · check traffic before leaving
Good to know: Michigan is on Eastern time, an hour ahead of Chicago; plan check-in and dinner times in local time.
