Live Entertainment

Enjoy Live Entertainment & Musicians as You Eat

Weekends at Oliver’s Dairy Bar & Grill mean live entertainment by local musicians. Sit on our deck and enjoy your meal, a cold beverage, or a delicious frozen treat and enjoy music by talented musicians from North Windham, CT, and the surrounding areas. Bring your family or friends and enjoy a night out.
To find out who is performing, check our Facebook page, or contact us: (860) 450-5555.


Bring your children to Oliver’s Dairy Bar & Grill and enjoy some time relaxing while they play in a safe space. We have a vinyl playscape available for the kids to climb on and enjoy. As you wait for your meal, your kids can enjoy swinging on the swings, playing in the playhouse, using the slide, and generally having fun. Let your kids run around while you relax and enjoy the evening.

Cornhole and Lifesize Jenga!

For the kid in you, enjoy a game of Cornhole and Jenga while you’re here!