Cumberland also looks good - gotta get there someday but will need to get an earlier start
There is a nice pedestrian mall with some good places to eat, but there is one interesting aspect. Many of the independent restaurants are closed on Mondays, including the BBQ joint right along the trail where the C&O and GAP meet. In 2020 I spent a Monday night at the Fairfield Inn during a cross-PA tour. You can literally ride on a paved path from the trail to the front door. (Got a great rate because of the pandemic.). Ended up walking a long way to a Mexican place for dinner.