Having lived on both lakes for most of my adult life, here's my take.
I love the big lake.....endless dining, shopping and fun destinations. Can get crazy on weekends so you must know boating rules and be on your toes at all times.
Winnisquam is much more peaceful. Even on a weekend you can find a sandy place to drop anchor (west side of the lake is mostly sandy) North end of the lake is has over a mile of undeveloped shore (preserve) so it's a quiet place to hang out.
Very small choice of restaurants and no access to any shopping really so there's not much to do except enjoy the lake.
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