Best Historic Restaurants in Westport

Simply our favorite spot for a romantic dinner to reconnect and share time and amazing food.

This place is fantastic! The food and service is five stars. Easy parking and on a cute street full of young people. It feels vibrant and Washington Prime feels cozy compared to other steakhouses. Save room for dessert … not your typical dessert menu … I’ve tried them all and they don’t disappoint. It’s worth every penny.

… A much-needed piano bar in Norwalk—an incredible spot for an unforgettable night!

This is the best Italian food anywhere in the state. Whenever I am in town, I make sure to come for dinner. It’s simply the best.

We love going to the Roger Sherman Inn. It’s very pretty, quiet and upscale. However, the last couple times we’ve been there the service has not been terrific. Not sure if they’re understaffed or if the particular waiter we had last night was new, but extremely slow. The owner was dining in the restaurant at the table next to us with her family. When they were finished with dinner, she was actually clearing plates and taking drink orders. I still love this restaurant.