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Published on December 17, 2025

What’s Happening Cape Cod - February 2026 What’s Happening Cape Cod

Even in the heart of winter, Cape Cod has plenty to offer. February brings good vibes, live music, a showcase of handcrafted boats and a favorite chocolate festival—perfect reasons to get out and enjoy the season.

Love Farms – Winterfest

Feb. 1, 8, 14, 15 & 21
Saturday and Sundays, 1-4 p.m. (check website for schedule)
607 Main St., West Dennis

Love Farms Winterfest concert series in February features live music from Nico Rivers, Sam Luke Chase, Dave Alves Band, Jarad Moore and the Classic Vibe Band. Bring a cozy layer, grab a drink or a farm-fresh bite from Love Farms’ dining and patio offerings, and enjoy an afternoon of good vibes and local sound on the farm.

The Boat Builders Show on Cape Cod

Jan. 30-Feb. 1
Hyport Conference Center
35 Scudder Ave., Hyannis

Visit the Boat Builders Show on Cape Cod to see beautifully crafted boats from independent builders, connect with the creators, and explore seminars and exhibitors dedicated to maritime craftsmanship. For details, schedules and exhibitor info, click here.

Annual Osterville Chocolate Festival

Saturday, Feb. 14
11 a.m.–2:30 p.m.
Osterville Village Library

Celebrate Valentine’s weekend with the Chocolate Fest Chocolate Baking Contest at the Osterville Village Library! Bring your sweet creations for judging — small entries (enough for three judges) should be dropped off at the library between 10 a.m. and 11:45 a.m. Prizes will be awarded, and all entrants receive a free chance to win a chocolate gift basket. Due to health guidelines, samples won’t be served after judging, but pre-packaged treats will be available. The chocolate festival also includes a dog parade and a special chocolate presentation (details below).

Valentine Dog Parade
11-11:30 a.m.

Meet on the Calvin C. Gould Library Green in Osterville for a festive dog parade through the village, with prizes and treats for participants. (Weather permitting.)

Special Chocolate Presentation
12:30-1:30 p.m.

Enjoy a free talk by Anthony Sammarco, “Chocolate: From the Chocolate of the Aztecs to Baker’s, Hershey’s, Cadbury, Schraffts and Toll House Cookies,” exploring the history and evolution of chocolate.

For questions, contact the library at 508-428-5757 or ofl_mail@clamsnet.org.

Ragtime, Blues, & All That Jazz – Cape Symphony

Feb. 21 & 22
7:30 p.m. Saturday; and 3 p.m. Sunday

Step into a world of toe-tapping rhythms with Ragtime, Blues, & All That Jazz, a CapePOPS! concert by Cape Symphony at the Barnstable Performing Arts Center. Byron Stripling returns to the Cape Symphony stage for a high-spirited journey through iconic American genres, blending masterful musicianship with his signature charm and storytelling. The program celebrates legends, including ragtime great Scott Joplin and blues icon Muddy Waters. Stripling is joined by keyboardist Bobby Floyd, whose career includes collaborations with Ray Charles, Dr. John and the Count Basie Orchestra.

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