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If you're looking for a smaller town/city, Cape May, NJ seems to fit what you're looking for. It's a summer resort town but in late September it's much less crowded and one of the best times to go. It's still warm, the ocean still warm enough to go into, and it's quieter at this time.
You can easily access it from Atlantic City International Airport (it's about 40 miles south) and pretty easily from Philadelphia International Airport (it's about 90 miles from Philly, so you would need to drive).
It is so worth it though.
If you're looking for a bigger city, I'd say Boston is probably your best bet.
I hadn't thought about that. It'd work good for Salem, but things to see (the things I liked) are kind of spread out. Is there a way, once you get to Concord to easily get out to places like Walden Pond, Sleepy Hollow Cemetery, etc.?
Concord is a little less compact/dense than Salem, but most of the major tourist attractions (National Historic Park/Old North Bridge, Sleepy Hollow Cemetery, Orchard House, etc.) are all within easy walking distance from the train station/downtown. Walden Pond is the only real outlier, as it's about a 35-minute walk.
Of course, if you bring a bike with you on the commuter rail... even better. Most people don't know about the Reformatory Branch Trail that runs through Concord and links up with the Minuteman Bikeway (which ends at the Red Line in Cambridge). Another option is to ride your bike along the Battle Road towards Lexington - this is the only other part of Concord that is tough to reach on foot.
If you're looking for something even less crowded and less expensive than Boston, but has a lot of the qualities you're looking for, Portland in Maine might be a good choice.
This list could be good for looking into places that you may want to visit: Great Places in America
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Most people don't know about the Reformatory Branch Trail that runs through Concord and links up with the Minuteman Bikeway (which ends at the Red Line in Cambridge). Another option is to ride your bike along the Battle Road towards Lexington - this is the only other part of Concord that is tough to reach on foot.
