Road Town, like the rest of the British Virgin Islands, does not have a lot of exciting nightlife; most people hang out at beach bars for drinks after dark. The best known nightclub in town (and throughout the Territory) is Bomba’s Shack, which has live entertainment on regular nights and a wild Full Moon Party once a month. Other notable bars and places to hang out during the evening are the Beach Club Terrace (284-494-2272), where guests can enjoy fusion cuisine by candlelight as they listen to live jazz performances, C&F Bar in Purcell Estate (284-494-4941) famous for curry, barbeque and seafood, Captain’s Table Café at the Inner Harbour Marina (284-494-3885), and Nexus Café, Bar & Grille, which features al fresco dining. Pusser’s Road Town Pub on Waterfront Street (284-494-3897) has nickel beer nights on Thursdays that never fail to gather a crowd. Quito's in Cane Garden Bay is the hotspot on Friday night. Quito and The Edge usually play on Friday and Saturday nights and Quito, a well known reggae artist ,plays solo on Tuesday and Thursday.

Swankier establishments in Road Town for fine dining and a pleasant evening include Callaloo on the Reef (284-495-3311) with gourmet Caribbean cuisine, Capriccio di Mare, an Italian sidewalk café, and Fusions (284-494-8041) at the Hotel Castle Maria overloading Road Town Harbour.

As this is the Caribbean, the national drink is undoubtedly rum. There are many good cocktails, and every beach bar is bound to serve up a wide variety of rum-based drinks. The most famous are the “Pain Killer” and “Bushwhacker.”