Maine Street 195 Main St, Ogunquit, ME, United States

Join us for an unforgettable Memorial Day Weekend extravaganza at Mainestreet Ogunquit!

📅 Date: Memorial Day Weekend 📍 Location: Mainestreet Ogunquit

Get ready to kick off summer with a bang as we present a lineup of electrifying events guaranteed to make your holiday weekend one for the books!

Come From Away

Ogunquit Playhouse 10 Main St., Ogunquit, ME, United States

Come From Away transports you into the lives of 7,000 stranded passengers and the inhabitants of the unlikely Newfoundland town that welcomed them. Cultures clash and nerves run high, but uneasiness turns to trust, and gratitude grows into enduring friendships through this vibrant musical score. On 9/11 the world stopped and a day later their stories moved us all.

Presented through special arrangement with Music Theatre International (MTI).

$40

Dueling Drag Divas

Maine Street 195 Main St, Ogunquit, ME, United States

LIVE SINGING! CELEBRITY IMPRESSION SHOW! Beyonce! Chappell Roan! Celine Dion! Taylor Swift! + DIRTY DIZNEE ROUND! Outrageously Offensive!

$25

Curbside Queens presents Taylor Swift Drag Night

Leavitt Theater 259 Main St, Ogunquit, ME, United States

The Curbside Queens take on your favorite pop princess! "Taylor Swift Drag Night" at The Leavitt Theatre has become an annual favorite!! Don't miss out on this incredibly fun night of all things TAYLOR!

$29

Come From Away

Ogunquit Playhouse 10 Main St., Ogunquit, ME, United States

Come From Away transports you into the lives of 7,000 stranded passengers and the inhabitants of the unlikely Newfoundland town that welcomed them. Cultures clash and nerves run high, but uneasiness turns to trust, and gratitude grows into enduring friendships through this vibrant musical score. On 9/11 the world stopped and a day later their stories moved us all.

Presented through special arrangement with Music Theatre International (MTI).

$40

Funny Ladies of Boston

Jonathans Listening Room 92 Bourne Lane, Ogunquit, ME

Funny Ladies of Boston brings together three of the sharpest, sassiest, and downright funniest women in comedy for one unforgettable night of laughs. Headlined by Amy Tee, known for her smart, candid wit and appearances on Logo TV and Comedy Central, this show serves up punchlines with heart and edge. Joining her is Stacy Kendro, a national comedy circuit regular with roots in both stand-up and sketch, whose quirky charm and fearless humor have made her a crowd favorite. Rounding out the trio is Annie Powell, a rising star whose vibrant energy and quick takes on everyday absurdities never fail to win over a room.

Whether you’re a die-hard comedy fan or just in need of a good laugh, Funny Ladies of Boston is the perfect way to shake off the stress and enjoy a night of top-shelf entertainment. Grab your tickets early—these ladies don’t hold back, and neither should you!

$31.5

Dueling Drag Divas

Maine Street 195 Main St, Ogunquit, ME, United States

LIVE SINGING! CELEBRITY IMPRESSION SHOW! Beyonce! Chappell Roan! Celine Dion! Taylor Swift! + DIRTY DIZNEE ROUND! Outrageously Offensive!

$25

Come From Away

Ogunquit Playhouse 10 Main St., Ogunquit, ME, United States

Come From Away transports you into the lives of 7,000 stranded passengers and the inhabitants of the unlikely Newfoundland town that welcomed them. Cultures clash and nerves run high, but uneasiness turns to trust, and gratitude grows into enduring friendships through this vibrant musical score. On 9/11 the world stopped and a day later their stories moved us all.

Presented through special arrangement with Music Theatre International (MTI).

$40

Neil Pearlman

Dance Hall Kittery 7 Walker St, Kittery, ME, United States

Neil’s deep love of the Gaelic music traditions has seen him welcomed into spaces that few other Americans have been. He was selected for the 2025 Shannon Residency at Beinn Mhabu in Cape Breton and has performed and guest lectured at the Irish World Academy of Music and Dance at University of Limerick, Ireland and the National Centre of Excellence in Traditional Music in Plockton, Scotland. His first solo piano album Refractions features frequently on BBC Radio nan Gàidheal and BBC Radio Scotland and his 2020 release with Shetland fiddler Kevin Henderson received 5 stars from Scotland’s national newspaper The Scotsman.

$22

Initials JR – Live Jazz

Leavitt Theater 259 Main St, Ogunquit, ME, United States

Incredible musicianship every Sunday with Initials JR. Come see some live jazz and enjoy dinner & drinks all in a 100-year-old theatre that's just moments from the sea!

$5

Karaoke at Maine Street

Maine Street 195 Main St, Ogunquit, ME, United States

Karaoke Fridays and Sundays 9pm til 1am!

Free

Shades of Blues

Jonathans Listening Room 92 Bourne Lane, Ogunquit, ME

Shades of Blue brings together some of New England's best R&B and Blues players

Fronted by Grammy nominated singer/guitarist Jon Butcher and award winning Blues Dive Diane Blue. The rhythm section features members of southern rockers Once an Outlaw

Don't miss this show as Shades of Blue only perform a hand full of shows annually as individual tour schedules and commitments make scheduling difficult.

$41.5

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