Through Meetup.com I discovered a support group for owners of fearful and reactive dogs. They do group hikes that they call "AwkWalks" which are basically a structured group activity where you can practice training and counterconditioning your dog in a non judgmental environment. Delilah and I went, and there was one other dog and owner, and then the organizer came without her dog. Anyone's allowed with or without a dog, and the dogs wear color coded bandanas- blue if they're friendly and yellow if they need space.
Delilah did so well and the other dog was very lovely too (I actually know her from the daycare I work at). It was really nice to be able to talk to other owners that face similar challenges with their dogs as me and Delilah. We also talked about the different trainers we've worked with in the area and training classes we've done. We're definitely looking forward to going on more of these hikes in the future!