History of the Inn and Downtown Annapolis

Our building was built on its Historic Foundation in 1899, on the grounds of the original Annapolis City Hotel (1788-1890), where George Washington lived for some time after he retired as Commander in chief.

It was originally the Germania Hotel, but soon became Bernstein’s Confectionary (Drug Store) and remained so until 1965, when sold to Charles (Chick) and Ruth Levitt.


1965 - 1990

The Scotlaur Inn was a dream come true for Chick and Ruth Levitt. Chick & Ruth supported their family with Chick and Ruth's Delly and a little rooming house with 12 rooms and only 2 bathrooms above the Deli. One of Chick and Ruth Levitt's many dreams were to establish a beautiful historic Bed & Breakfast Inn. However they never had the resources to make that dream come true. Our building was built on its Historic Foundation in 1899. It was the site of the original Annapolis City Hotel, from 1788 to 1890. On this site George Washington lived for some time after he retired as Commander in chief. Six months after Ruth passed away in 1986, there was a large fire in the rooming house above Chick and Ruth's Delly. Chick and Ted rebuilt and remodeled the entire upper level to be the Scotlaur Inn Bed & Breakfast, named after Chick and Ruth's grandchildren Scott and Lauren.


1990 - 2017

Ted Levitt grew up working in the family businesses. He was only away for a few short years while attending college. One of Teddy's many fine accomplishments was graduating from the Culinary Institute of America and Florida International University. Beth joined the family in 1981 has a passion for tennis, having played for Rollins College in Florida and for the University of Maryland. Ted and Beth raised two adored children, Scott and Lauren, for whom the Inn was originally named. Ted continues to join ‘the regulars’ on many a morning.


2017-2021

When Keith became owner of Chick and Ruth's and the Scotlaur Inn in 2017, he made local history by becoming the first African American owner of an Annapolis Main Street business.

Keith passed away unexpectedly in early 2021, just after renovating the Inn during the pandemic to its current state, and etching its new name, the Inn on Main, in glass on the front door. To restaurant and Inn staff, he was a thoughtful leader and mentor. They remember with love and humor his orders of "chicken noodle soup with no chicken". Under Keith’s leadership, the restaurant served as a community for patrons and staff alike.

His beloved son, Spencer, and partners and friends of the family, Mathew and Lisa Taylor, are dedicated to continuing to provide local hospitality and great food to Annapolis visitors and locals. We welcome you!