Yes, you would have to get a DBR at every turn around, (a corner in your ride). Even assuming that you can get all the required photos for this ride in that 40 mile loop, repetitive rides are frowned upon and require extra documentation and pre-approval. Plus, the Thanksgiving Gold ride requires the photos to be taken 150 miles apart. Typically that is riding miles, but the spirit of that rule is to go somewhere different for each picture. Even using Spotwalla, you are still required to document each "corner", which would require a DBR at every turn around, which adds a lot of time when you're doing it every 20 miles. Note that DBRs don't have to be fuel, any computer generated receipt with the correct info is acceptable.
From the link below:
Rules
Photos are required for this certificate. Each photo must include your motorcycle except for selfie photos of you eating food items. Get a DBR in the same city of each photo. When using a selfie photo of you eating as one of your photo requirements, obtain and submit your DBR for that food item purchase.
Required photo possibilities:
-- your motorcycle with a post office, water tower, welcome to (town) sign, DOT town sign or DOT street sign which includes the word Plymouth, Mayflower, Pilgrim, harvest, turkey, corn, beans, pumpkin, potato or cranberry. harvest is not a common name so we will accept photos with your motorcycle in front of church signs with harvest in its name. Furthermore, Mayflower is not a common name so we will accept photos with your motorcycle in front of a sailing vessel. Remember, get a DBR in the same city of each photo.
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*****Each photo must be at least 150 miles from the previous photo****
Thanksgiving rides have many different levels of difficulty.
Thanksgiving 1000 - Provide 2 different required photos - 24 hours
Thanksgiving 1000 SILVER - Provide 4 different required photos - 24 hours
Thanksgiving 1000 Gold - Provide 5 different required photos PLUS a selfie of you eating a peice of pumpkin pie. You must supply a DBR from the restaurant. -24 hours
Different is defined as different words, i.e. turkey, potato, Plymouth, etc
Thanksgiving Ride rules