Having an interesting destination is always an incentive. Whether that is a cafe stop or a site of historic interest or a spectacular viewpoint, try to plan a few into your route. And don't forget to get a photo for the Photo of the Month competition. The map on the Cafe Guide is a good starter for direction and distance. There is also a spreadsheet of routes down below.
Distance, Climbing and Duration. Choosing your duration is affected by the distance and climbing in a route. Think about the ride category - short flat Black rides will be faster than long hilly Black rides. Consider the roads you are using here - pretty country lanes are slower than 'main' roads. Think about the likely weather - lanes will get messy in wet weather and icy in cold weather - main roads may be clear but road spray may be an issue
Most likely you'll use a GPS based cycling computer to give turn by turn instructions, but if you don't then consider how many turns your route will require. Built up areas are harder to navigate than open roads in the countryside. Simpler routes mean more chatting time and less need to concentrate. If you use an auto-routing option when planning your route, make sure you zoom in to check turns - Garmin Popularity routing often sends you round roundabouts the wrong way in Bracknell!
Choosing a convenient start and finish point is important - while starting in Peach Place on an early Sunday morning is sociable it's not necessarily the best start point midweek. Starting away from Wokingham may give you more options for routes. Remember members live all over the area! You can also finish the ride before getting back to the start if that is more convenient for members to peel off home.
Think about where you might need to change the route mid ride in certain situations. Consider quick main road or flat options if you are running out of time or riders are tiring. Train stations are good for serious ride ending mechanicals.
The best thing to do is to ride your route before your group ride. If you can't do that then use Google Street view to step through the route to check junctions. The web version of Google Maps allows you to import a GPX file to create a map in My Maps (look under Saved Maps). Create a New Map, Add a layer and Import your GPX file, then browse the Street View images. Check for road closures here
Guide to common cafe destinations with popular routes