Three different date nights in Winnetka and Lake Forest
Start with the evening you want: a courtyard bistro dinner, Vietnamese food with a dressier setting, or sushi and pub dishes at the same table. These three options give you a reason to choose one over another.
By Loktin · Sources checked September 23, 2026
Winnetka · 844 Spruce Street
Pomeroy: make the setting part of dinner
Choose Pomeroy when you want a French bistro and a choice of settings: the restaurant has a dining room, bar, sidewalk café and garden courtyard. The courtyard is the reason to put this one on your list if an outdoor dinner is the plan.
For a daytime date, Pomeroy also lists weekend brunch. That makes it an option when dinner does not fit your schedule, without switching to a different restaurant.
Decide before booking: courtyard or indoor table. Ask about the seating area when reserving; a reservation alone does not establish which space you will get.
Le Colonial is the choice here for Vietnamese cooking and a more dressed-up evening. Its Lake Forest restaurant occupies a two-story building in the Market Square district, with dining spaces, a garden and a bar.
The restaurant explicitly requests refined dinner attire. If your plan starts with an outdoor activity, build in time to change rather than assuming the same clothes will suit both stops.
Decide before booking: review the Lake Forest menu and dress code together. Use the Lake Forest location’s reservation form, not the Chicago location.
The Bar at Deer Path Inn: when you want different things
One of you wants sushi; the other wants soup, a salad or pub food. The Bar’s published offerings span both: French onion soup and Cobb salad sit alongside spicy tuna rolls, seaweed salad and sashimi. That range is its practical advantage for an indecisive pair.
Deer Path Inn has several dining venues. The Bar is a specific choice, distinct from The Brasserie, White Hart Pub and Afternoon Tea. You do not need to be staying at the hotel to dine there.
Decide before going: name The Bar when arranging dinner. A booking or menu for another Deer Path Inn venue is not interchangeable.