Look up a local Astronomy club.
Chances are very good that they have equipment, regular meetings and stargazing parties. Some clubs have telescopes you can check out, like library books.
Being in Boston, There should be active astronomy clubs affiliated with local colleges and universities. Contact the science buildings/departments and they should have a wealth of contacts for you.
Personally, I started with an Orion 8" Dobsonian. Works great, but can be a bit clunky to move around and it doesn't track automatically. ( new ones have the hardware to do that for the $$$ )
Bottom line is there are a whole lot of considerations before dumping bucks in a scope. You'd be doing yourself a favor to spend time with the different varieties before committing.
Good luck!
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