I'm thinking something like
this for Saturday's ride. Out Spring Street (to make up for lost years, now that it's paved) to Haydenville, up north to Conway past the various reservoirs, up either Lower or Upper Rd as the fancy strikes us to Greenfield, then back home via Montague as if on both the Tuesday time trial and the Wednesday night. Only, you know, considerably slower.
No food stop designated - that will be a game-time decision (you can begin to prepare your arguments now for Greenfield Coffee, the Book Mill, Wild Roots, or some wildcard) based mostly on the sumptuousness of my repast Saturday morning. The key feature of this ride is that it largely avoids higher education move-in traffic. (Also we unhitched a rider near the reservoir on Webber Rd a few weeks ago and no one has seen them since, so we'll all be doing a little recon as we climb.)