Oh please do come! It's a lovely town whether it's summer, winter, spring or fall. There's always something going on in town: Fall into St. Michaels, The Wine Fest, Christmas in St. Michaels, FREE concerts in the park (summer), programs, etc. at the museum -- lots to do. It's a little quieter with less traffic, certainly, but still plenty active. Although some of the restaurants in-town close usually January to February (sometimes even part of March), there are still restaurants nearby that stay open year 'round. And it's not unheard of for a restaurant to open on a really nice weekend weather-wise. Easton is just about 10 minutes away with a movie theater, lots of shops, art galleries, big-name retailers (Target, JC Penney, Lowe's, etc.), plenty of restaurants to choose from and more. Annapolis is about 45 minutes away if you want to have a "city" day. You surely won't have time to be disappointed!
Please feel free to email me direct as I'd be happy to help you in your relocating process.