This pilot study aimed to evaluate the perceived impact of therapeutic recreation activities for Persons with Dementia (PwD) on the groups' participants and on the staff running the groups in order to enhance the understanding of factors which impact the outcomes of therapeutic recreation. Ten therapeutic recreation staff (TRS) members led two series of 10 different group activities for 104 PwD. Afterward, they reported the activities they deemed most versus least successful for participants and for themselves. These evaluations were compared with observations of outcomes (attendance, engagement, affect) as rated by both TRS and research observers immediately after the activities. Choral-singing and brain games were most frequently reported as most successful for participants; holiday newsletter and creative storytelling were most often mentioned as least successful. Activities reported to be more successful for participants were also likely to be considered more successful for TRS. This work provides insight for future investigation on the variables affecting the impact of group activities on both the target audience and on the staff running them.