Shared leisure activities are important for family life but difficult to do with people who live far away. To explore how family and friends might be able to participate in outdoor leisure activities together over distance, we prototyped a shared bicycling technology probe using mobile video streaming. We conducted a study where half of our participants used our technology setup as a parallel experience where both cycled at the same time. The other half used it to connect a bicycler with a person at home. Participants highly valued the experience and the video and audio connections allowed to them to feel closely connected with their partner. Conversations typically focused on everyday activities, rather than the activity itself. Challenges immerged including difficulties in looking at the video feed while riding, boredom during longer rides, and feelings of obligation to make eye contact. Safety was not seen as an issue but this was more of a perception. These findings suggest important considerations for the design of video streaming technologies for shared outdoor activities.