Pepper's Kaleo Wassman plays Pickles Pub on Thursday, Nov. 12

The reggae-rock frontman brings his solo show to an 8th Street bar in the off-season, with Milton J opening and $10 tickets.

In November, Ocean City belongs to the people who stay here year-round, and those are the people who'll fill Pickles Pub next Thursday. Kaleo Wassman plays Pickles Pub on Thursday, Nov. 12, with the show starting at 7 p.m. Milton J opens, and tickets are $10 through Eventbrite.

That's a small price and a small room for this artist. Wassman usually headlines rooms of about 500, so getting him at a neighborhood bar on Philadelphia Avenue is a good off-season deal.

If the name is new to you, his band won't be. Wassman is the lead vocalist and guitarist of Pepper, the reggae-rock trio he plays in with Bret Bollinger and Yesod Williams, per Wikipedia's Pepper entry). His solo career is newer. He started releasing music under his own name with the single "Shine Again," a more introspective turn according to The Pier. His early solo dates were acoustic shows in Dana Point and San Diego, The Pier reported in an interview about the project. A full album, *Say Yes*, followed in 2026 on LAW Records, per its streaming listing, which says the record lets him draw on his soul and R&B roots.

That means this probably isn't a Pepper show with a different name on the poster. Expect the solo material, and the reggae this bill is filed under.

Getting him at a neighborhood bar on Philadelphia Avenue is a good off-season deal.

The room is easy to love. Pickles Pub at 706 Philadelphia Ave. has been a local hangout for drinks, food, entertainment and sports since it opened in 1989, and Justin and Brittney Acita bought the 8th Street bar in 2015, the Maryland Coast Dispatch reported. It's also where the pickle shot made its name; the bar serves about 100,000 a year, WJLA reported. Whether you order one before the set is up to you.

A few notes. With a 7 p.m. start on a Thursday, there's time for dinner first and you'll be home at a reasonable hour. Tickets are through the Eventbrite link on our listing, and at $10 it's worth buying ahead rather than chancing the door. Pickles is open daily from late morning until 2 a.m., so there's no rush to leave after the last song.

A frontman people know, a new solo record and a $10 ticket on a quiet November night. That's what the off-season is for.

Sources: Pepper (band) — Wikipedia (en.wikipedia.org); Kaleo Wassman — Wikipedia (en.wikipedia.org); Kaleo Wassman Releases Debut Solo Single 'Shine Again' (The Pier) (thepier.org); Kaleo Wassman Talks Solo Project and Yoga Retreat (The Pier) (thepier.org); Say Yes — Kaleo Wassman (HighResAudio) (streaming.highresaudio.com); Pickles Pub (Maryland Coast Dispatch) (mdcoastdispatch.com); Pickle shots? Ocean City restaurant serves about 100,000 a year (WJLA) (wjla.com); Kaleo Wassman at Pickles Pub tickets (Eventbrite) (eventbrite.com)