Kickininee Provincial Park and Peach Orchard Beach are two popular spots for sunset watching in Summerland. Both locations offer unobstructed views of the lake, making them ideal for an evening picnic or a relaxing stroll while the sun sets over Okanagan Lake​.

During the summer months, Music in the Park offers free outdoor concerts, typically on Wednesday evenings at Memorial Park. This is a family-friendly event featuring local bands, making it a great way to enjoy the local music scene.

You can paddleboard, kayak, canoe, go boating or swim in the evening at your leisure. You can also rent paddleboards, kayaks, or boats from SWR Boat & SUP Rentals, located along the lakeshore. Evening rentals are available, allowing you to explore Okanagan Lake at a quieter, more peaceful time of day.

Shaughnessy’s Cove offers lakeside dining with beautiful views of Okanagan Lake. This restaurant is perfect for an evening meal while watching the sunset. Oak Estate Winery also provides outdoor dining with panoramic views of the vineyards and the lake​.

The Kettle Valley Steam Railway occasionally offers special evening or twilight rides during the summer and on holidays. These evening excursions allow passengers to experience a scenic ride through the Okanagan Valley at dusk​.

Summerland's clear skies and low light pollution make it a great place for stargazing. Popular spots include Peach Orchard Park and Giant’s Head Mountain, where you can enjoy expansive views of the night sky​.

Giant’s Head Brewing and Detonate Brewing are popular spots that stay open into the evening, allowing visitors to enjoy craft beers with a relaxed, social atmosphere. Both breweries often host community events or live music in the evenings​.

Families can enjoy an evening walk along Peach Orchard Beach or visit Memorial Park for a relaxed evening outdoors. Additionally, some local events, such as Light Up Summerland during the winter months, are family-friendly evening activities​.