Matt and I were invited to go caroling in SoCe with a group from Legacy Ministries. It was fun and definitely a good way to connect with some neighbors. We would do it again. However, one observation we made was the awkwardness people sometimes felt because they did not know what to do while being sung to. A few families brought their kids out on the porch to listen. A previous year we gave out books to kids. That was helpful because kids enjoyed choosing a book and it was something to do. To minimize the awkwardness this year we just sang one song at each house and then finished with "We Wish You a Merry Christmas" as we walked away.
Despite the awkwardness, people of all ages responded positively and thanked us for singing. After having a few houses where people were clearly home, but did not answer the door, we decided to go to the houses that had most decorations and lights. We theorized that those folks must at least enjoy the Christmas season.
We learned that it is helpful to have the following: at least 2-3 strong singers in the group, a leader who chooses the songs and verses to sing at each house, songbooks - at least one for every two people, and small battery-powered reading lights or flashlights. It also works better if you are somewhat acquainted with your neighbors - if they at least recognize a familiar face, they may be more comfortable.