Best Places to People Watch in Rehoboth Beach

Go on, admit it! Shhh! We won’t tell! We all love to sit and people watch. Here’s our favorite places in Rehoboth Beach to sit and watch the world go by! Grab a cocktail or some food and make it a party!

  1. Top of The Pines, The Pines Rehoboth. Located at 56 Baltimore Avenue. One of Rehoboth’s newest restaurants and already stealing a piece of our heart! You can eat from their great restaurant menu outside on their first floor deck, but our favorite place is the second floor verandah at The Top of The Pines, the restaurant’s exhibition and cabaret space. Grab one of their creative cocktails and watch the fun on Baltimore Avenue, and the outdoor deck at Aqua Grill opposite!
The second floor deck at The Top Of The Pines. Lovely at night. Perfect for people watching day and night!

2. The bar windows at Henlopen City Oyster House. Located at 50 Wilmington Avenue. Sit in a fish bowl, watch and be watched! Wave to friends old and new while enjoying some of the freshest fish dishes and rotating selection of craft brews in town. Our guilty secret – as locals, we prefer to eat in the bar than the restaurant side!

Henlopen City Oyster House. Enjoy the A/C and in winter, the heat. In any season, nab a seat in the bar windows!

3. Obies By The Sea. Located at 1 Olive Avenue on the North Boardwalk. Under new management and renovated for 2019. We go for the view and love to eavesdrop on boardwalk conversations – more drama than an episode of The Real Housewives!

Obies By The Sea. That view!

4. Aqua Grill. Located at 57 Baltimore Avenue. A large outdoor deck pulls a colorful crowd. We like it best lunchtime or early afternoon before the crowds come off the beach. Relax with a early happy hour cocktail and watch the beachgoers returning.

The deck at Aqua Grill gets crowded for sure. See and be seen!

5. The rooftop dining space at The Cultured Pearl. Located at 301 Rehoboth Avenue. A long time staple in Rehoboth Beach. Make a reservation and nab an outdoor table on the roof overlooking one of the best vantage points along Rehoboth Avenue. Only two stories high so you can even hear sidewalk conversations and spot friends!

The outdoor rooftop dining ‘room’ for The Cultured Pearl. One of the nicest outdoor dining experiences in Rehoboth Beach.

Looking for the perfect vacation rental to people watch? Here’s a couple:

  • Stay Brit at 24 Rehoboth Avenue, Rehoboth Beach has the best second floor loft overlooking the bandstand and all the action on Rehoboth Avenue just steps from the boardwalk and beach. In hot weather, you can relax in air conditioned comfort and listen to the sounds and crowds enjoying the summer concert series at the Rehoboth Beach Bandstand. In colder weather, hop on the availability and nab this property for a birds eye (heated) viewpoint on all the off-season events such as Seawitch Festival, and the lighting of the Rehoboth Beach Christmas tree festival.