Systems and methods may be provided for alerting a user of an obstruction to a bicycle mounted on a vehicle. An obstruction sensing device may be provided that may be mounted on the bicycle. The obstruction sensing device may include an engagement mechanism configured to attach the obstruction sensing device to a bicycle, an emitter configured to emit a detection signal, a receiver configured to receive a reflection of the emitted detection signal that may indicate an obstruction, and a transmitter configured to transmit an alarm signal when the reflection is received by the receiver. In some embodiments, a remote may be provided that may alert a user.