This study uses questionnaires to explore the obstacles and negotiation strategies faced by middle-aged and elderly people engaged in leisure activities. The results show that the main factors of leisure obstruction for middle-aged and elderly people are time hindrance, followed by peer obstruction, facility accessibility hindrance, and relatively low internal barriers. The most commonly used leisure negotiation strategy facets are interpersonal negotiation strategies and time negotiation strategies, skills negotiation strategy, and money negotiation strategy. Middle-aged people with different health status and marital status have significant differences in leisure barriers, middle-aged people with different health status, marital status, and income status have significant differences in negotiation strategies; at the same time, leisure obstacles can significantly affect leisure negotiation strategies. This study suggests that related governmental organizations should conduct a survey of recreational needs and recreational barriers for middle-aged and elderly people and actively provide them appropriate leisure participation resources.