A tent system including a first tent section having a first transition border. The first transition border is configured to receive a first support member at a first transition height. The first transition border has a first transition width. A first transition section is defined by the first transition border and a second transition border. The second transition border is configured to receive a second support member at a second transition height. The second transition border has a second transition width that is less than the first transition width. A flexible roof is configured to cover the first tent section and the first transition section. The flexible roof is configured to be supported by at least the first support member and second support member. The flexible roof is configured to cover the tent system.