Clarkston Date Night
8 stops · about 4 hours · Updated October 6, 2026
Build a date night in Clarkston, MI around Italian dinner, a cocktail and ice cream mixed to order. Start at Bologna Trattoria on Dixie Hwy, where the quiet, cozy setting includes family photographs and a history rooted in Detroit. The menu offers comfort food, small plates and vegetarian options, and reservations are accepted. For another dinner choice, Kruse's Deer Lake Inn pairs seafood and hot bread with a homey, rustic setting; its on-site bar also serves cocktails.
Make Outback Steakhouse your cocktail stop. Its bar serves cocktails, beer, wine and liquor, with happy-hour drinks available. Then finish at Cold Stone Creamery on Sashabaw Rd with a design-your-own creation hand-mixed on a granite slab or a shake. The shop stays open until 9:30 p.m. Friday and Saturday and 9 p.m. the rest of the week.
For a planned sweet treat, arrange an appointment with Clo's Cakery for custom cakes or cake pops, with pickup and delivery available. Keep Sisters Cafe for a daytime date: its breakfast, brunch and lunch service ends at 3 p.m. daily.
Dinner
evening
Stop 1
Bologna Trattoria
4.6(347)Village of Clarkston
Bologna Trattoria anchors dinner with quiet, cozy Italian dining, family photographs on the walls, vegetarian options and an on-site bar serving cocktails.
Stop 2
Sisters Cafe
4.6(217)Village of Clarkston
Sisters Cafe provides a daytime date option with breakfast, brunch, lunch and coffee in a casual, cozy setting, closing daily at 3 p.m.
Stop 3
Kruse's Deer Lake Inn
4.5(1805)Village of Clarkston
Kruse's Deer Lake Inn brings seafood and hot bread to dinner in a homey, rustic setting, with cocktails and desserts also available.
Cocktails
evening
Stop 4
Fountains Golf & Banquet
4.4(711)Village of Clarkston
Fountains Golf & Banquet adds an activity option with nine-hole and eighteen-hole golf, golf carts and food served at the same location.
Stop 5
QDOBA Mexican Eats
4.4(1007)Village of Clarkston
QDOBA Mexican Eats offers a takeout alternative with customizable Mexican food, vegetarian options and dessert, plus delivery for plans away from the restaurant.
Stop 6
Outback Steakhouse
4.3(3641)Village of Clarkston
Outback Steakhouse earns the cocktail stop with an on-site bar serving cocktails, beer, wine and liquor, alongside happy-hour drinks and steakhouse fare.
Something sweet
night
Stop 7
Clo's Cakery
5.0(175)Village of Clarkston
Clo's Cakery supplies a planned sweet treat through appointment-only service, offering custom cakes and cake pops with curbside pickup and delivery available.
Stop 8
Cold Stone Creamery
4.7(89)Village of Clarkston
Cold Stone Creamery finishes the evening with design-your-own ice cream hand-mixed on a granite slab, shakes and Friday and Saturday hours until 9:30 p.m.
