Reddit reviews New York Atlas and Gazetteer
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Amazingly detailed and beautifully crafted, large-format paper maps for all 50 StatesTopographic maps with elevation contours, Major highways and roads, dirt roads, trails and land use dataGazetteer section contains information essential for any outdoor enthusiast, such as points of interest, landmarks, scenic drive recommendations and more (Note: available information varies by State)Perfect for sightseeing, exploring back roads, outdoor recreation and trip planning
One of my favorite roads in all of NY is State Route 30. Tons of great scenery to drive through in the Catskills and Adirondacks, and not too far off from Rt 30 are some state campgrounds like Beaverkill and Indian Lake. Judging from your proposed locations (I'm assuming in chronological order) Rt 30 would be a good way to start, going North. Centering your northbound trip along Rt 30 may help you pick out locations, attractions, etc. A 45 minute drive East of Rt 30 in Tupper Lake, you can go to Lake Placid to experience some winter olympics-related attractions or simply bask in the High Peaks region. There's plenty to do in Lake Placid in the way of eating, staying, and doing all year-round.
The return trip South to hit your desired locations, I would take State Route 3 from Tupper Lake in the Adirondacks to Watertown or possibly further to Fulton, which is within arm's reach of Syracuse. If you want to expedite your drive to Syracuse, take I-81 from Watertown. Once you arrive in Syracuse, meandering through the Finger Lakes Region is all really a matter of preference for you. I will point out that the Glenora Winery just North of Waktins Glen is a winery (and hotel!) worth a stop.
For lodging, I would start by mapping out NY State Campsites along your route. Be mindful that campsites (epsecially Watkins Glen) book out several months. I've personally had reservations for Watkins Glen 4 months ahead.
Another possible resource you may be interested in is the New York Atlas and Gazetteer. It's a BIG BOOK (11 x 15 inches) of all of NY. I recommend this not just for the highly detailed maps, but for the list of recreational activities, campsites, hiking trails, and other points of interest. I personally keep a copy of this in my car between my seat and the center console. BONUS: No internet connection required!
EDIT: Some state campsites have designated walk-on spots which cannot be reserved ahead of time. I've had some luck in the past with this and it's worth a shot if you're short on time. Try calling each site's office ahead of (1 day or day-of) your arrival to confirm availability.