Events

Despite (or perhaps because of) living in such an isolated place, Rupertites have become experts at filling their free time with events and activities. On any particular weekend, it’s easy to participate in live music, events, festivals, and more.

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CHSS Presents Almost, Maine

Dec 4

CHSS Presents Almost, Maine

7:30 pm – 10:00 pm
Karaoke Night at the Moby Pub

Dec 4

Karaoke Night at the Moby Pub

10:00 pm – 11:30 pm
Winter Fest 2025

Dec 5

Winter Fest 2025

December 5, 2025 @ 10:00 am – December 7, 2025 @ 5:00 pm
Shop Local Holiday Passport

Dec 5

Shop Local Holiday Passport

December 5, 2025 @ 10:00 am – December 21, 2025 @ 6:00 pm
Jingle Boat Express

Dec 5

Jingle Boat Express

12:00 pm – 3:00 pm
2nd Annual Crab Trap Christmas Tree Lighting & Celebration

Dec 5

2nd Annual Crab Trap Christmas Tree Lighting & Celebration

6:00 pm – 8:00 pm
CHSS Presents Almost, Maine

Dec 5

CHSS Presents Almost, Maine

7:30 pm – 10:00 pm
Karaoke Fridays

Dec 5

Karaoke Fridays

9:00 pm – 11:30 pm
Breakfast with Santa!

Dec 6

Breakfast with Santa!

8:00 am – 11:00 am
Winterfest Family Bella Artes

Dec 6

Winterfest Family Bella Artes

1:30 pm – 4:00 pm
CHSS Presents Almost, Maine

Dec 6

CHSS Presents Almost, Maine

2:00 pm – 5:00 pm
Winterfest Outdoor Market

Dec 6

Winterfest Outdoor Market

5:30 pm – 8:30 pm