I need to get a new license. While my license does not expire until Feb. 2020, I want to get it done before I go to Canada in the fall and realize I have to get the upgraded version. Can you do that in Milford, or do I need to go to Nashua?

You can do it in Milford just bring your birth certificate, SS card (not laminated) and proof of residency which can be your current driver's license, registration, electric bill, lease or property tax bill. However if Saturday mornings work better, you can do it in Nashua the 2nd Saturday of each month from 8-12

Either does it, you need additional documentation for the Real ID, however you probably need a passport or card for going over the border.