Naples Hammondsport
If you like big long climbs and great views (they go together, right?) you will love this ride. It's 57 miles of either up or down. The big climbs are out of Naples and Branchport, but the long descents are out of Pultney and Italy Turnpike. Taking the alternate route from Hammondsport back the way you came is initially a climb, but once on the ridge the views are worth it. There would also be less traffic than following the shoreline but then you don't get to see all the cottages either. Food can be found in Prattsburg and again in Branchport (if you follow the lakeshore). The little store at the bottom of Italy Turnpike is open if you get there early enough in the day on Sundays.