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Live Events in Castine, Maine

Castine, Maine has 4 venues with upcoming events — bar & pub, historical society and gallery. 30 events are on the calendar, at spots like Pentagoet Inn & Pub, Castine Historical Society, Gallery B.

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This Weekend in Castine

Damariscotta Pumpkinfest & Regatta—oh my gourd, this is the Midcoast’s funniest, quirkiest fest for the giant gourd. This year’s event is held on
Pentagoet Inn & Pub
Fri, Oct 9
Damariscotta Pumpkinfest & Regatta
Pentagoet Inn & Pub
Fri, Oct 9
Damariscotta Pumpkinfest & Regatta—oh my gourd, this is the Midcoast’s funniest, quirkiest fest for the giant gourd
Pentagoet Inn & Pub
Sun, Oct 11

Coming Up in Castine

Death by Drowning: Castine Town Cemetery Tours (Date 1)
Castine Historical Society
Thu, Oct 15 · 10:00 AM
Castine, Penobscot Bay, and Global Slavery in the Age of Sail with Dr. Kate McMahon
Castine Historical Society
Thu, Oct 15 · 6:00 PM
Death by Drowning: Castine Town Cemetery Tours (Date 2)
Castine Historical Society
Sat, Oct 24 · 10:00 AM
Free Community Lunch & Raffle
Wilson Museum
Thu, Oct 29 · 11:30 AM
HallowWINE costume party
Pentagoet Inn & Pub
Fri, Oct 30
SWS26 • Art For Right Now 2026 • : The Small Works Show
Gallery B
Sat, Nov 21 · 9:00 AM
Small Works Show — new works drop
Gallery B
Sat, Nov 28 · 9:00 AM
Annual Pentagöet Christmas Party! On Friday, December 4
Pentagoet Inn & Pub
Fri, Dec 4 · 5:00 PM
Small Works Show — new works drop
Gallery B
Sun, Dec 6 · 9:00 AM
Annual CHS Sip and Shop
Castine Historical Society
Thu, Dec 10 · 3:00 PM
Small Works Show — in-person exhibit closes
Gallery B
Mon, Dec 21
The Mardi Gras Dinner Feast
Pentagoet Inn & Pub
Wed, Feb 17, 2027
The Mardi Gras Dinner Feast (Fat Tuesday pop-up)
Pentagoet Inn & Pub
Tue, Feb 23, 2027 · 6:00 PM
The Dinner of Five Flags
Pentagoet Inn & Pub
Sun, Mar 7, 2027 · 5:00 PM
The Titanic Dinner
Pentagoet Inn & Pub
Mon, Apr 12, 2027 · 5:00 PM
Maine Maritime Academy Graduation
Pentagoet Inn & Pub
Sun, May 2, 2027
Wings, Waves & Woods
Pentagoet Inn & Pub
Thu, May 13, 2027
Castine’s Memorial Day Weekend
Pentagoet Inn & Pub
Sat, May 22, 2027
The Acadia Birding Festival
Pentagoet Inn & Pub
Fri, May 28, 2027
The Guild School
Pentagoet Inn & Pub
Sun, Jun 13, 2027
Pentagöet Day!
Pentagoet Inn & Pub
Sun, Jun 27, 2027
Castine’s Fourth of July Pentagöet BBQ
Pentagoet Inn & Pub
Sun, Jul 4, 2027
Bastille Day in Castine
Pentagoet Inn & Pub
Wed, Jul 14, 2027
The Castine House & Garden Show
Pentagoet Inn & Pub
Sat, Jul 24, 2027
The 2nd annual Art Under the Elms festival
Pentagoet Inn & Pub
Sun, Jul 25, 2027
The Maine Lobster Festival
Pentagoet Inn & Pub
Thu, Jul 29, 2027
Castine Classic Yacht Race
Pentagoet Inn & Pub
Fri, Jul 30, 2027

Venues in Castine (4)

Pentagoet Inn & PubBar & Pub
21 events
Castine Historical SocietyHistorical society
4 events
Gallery BGallery
4 events
Wilson MuseumMuseum
1 event
Listings for Castine, Maine are compiled from public sources, each named with the site it came from and dated with the last time we read it. Details can change — confirm with the venue before you go. How we collect & verify.