First stop: Rent electric bikes at Pedego Electric Bikes on Main Street. They will help you make your route selection from easy and not-so easy bike routes. The electric bike is a great equalizer, and there are even tandem options.
Next: Woodlands Market for picnic supplies to pop into your bike basket. If you're biking Old Rail Trail to Blackie's Pasture, there are lots of bayside benches and a playground (with a view, naturally) to set up your picnic.