Walking in Westport, Connecticut, can be a mixed experience depending on the area. The downtown area offers a pedestrian-friendly environment with sidewalks and access to shops, restaurants, and cultural spots, making it relatively easy to explore on foot. However, much of the town is more suburban and spread out, with limited sidewalks in some neighborhoods, which can make walking less practical for reaching certain destinations. Weather conditions, typical of New England, may also influence the comfort of walking, especially during colder months or inclement weather. For short distances in central areas, walking can be a convenient option.

Andare in bici a Westport presenta alcune difficoltà a causa delle limitate infrastrutture per le bici. La disposizione della città e i percorsi minimi adatti alle bici possono rappresentare una sfida per la navigazione in modo sicuro ed efficiente. Sebbene alcune aree possano essere accessibili in bici, la mancanza di piste ciclabili dedicate o di ampi sentieri potrebbe rendere alcuni percorsi meno pratici. Inoltre, le distanze tra le destinazioni principali potrebbero richiedere un'attenta pianificazione per i ciclisti.

Public transportation in Westport includes buses and an on-demand shuttle service. The Coastal Link bus operates along the Route 1 corridor, connecting Westport to nearby towns. Additionally, the Wheels2U shuttle provides flexible, on-demand rides within the area, including access to train stations. While public transit can be a convenient way to travel locally, the town’s suburban layout may require some planning to ensure stops align with destinations. The infrastructure supports these services, but distances between stops and destinations might make walking less practical in some areas.