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Published on April 12, 2026

What’s Happening Cape Cod - May2026What’s Happening Cape Cod

Spring is in full swing on Cape Cod, and May is packed with events that celebrate the season, community and connection, including the vibrant Brewster in Bloom festival and meaningful gatherings like the Sharing Kindness walk—an event CCHC is proud to sponsor.

Brewster in Bloom

May 1-3

Celebrate the season at the 40th annual Brewster in Bloom! This year’s theme is Brewster Beach Day. The festive weekend features the 5K Bloom Run (10 a.m. on May 2), an arts and crafts fair (May 2 and 3), the beloved Bloom Parade (stepping off at 1 p.m. on Sunday, May 3), and lively happenings all around town. With colorful flowers, live entertainment and fun for all ages, it’s a joyful way to welcome spring on Cape Cod.

Comedy Night Fundraiser

May 14
Chatham Orpheum Theater, 637 Main St., Chatham

Get ready for a night of laughs that give back! Join us for a comedy night fundraiser featuring Amy Barnes—back by popular demand—for an evening of stand-up to benefit Cape Cod Hospital’s Family Birthplace. 

Choose from two showtimes (5 p.m. or 7 p.m.) and enjoy a fun, high-energy night at the Orpheum Theater. Seating is first-come, first-served, and tickets are expected to sell out—so don’t wait! Tickets are $65 apiece.

Rhododendron Festival

May 15-25
10 a.m.-5 p.m. daily
Heritage Museums & Gardens, 67 Grove St., Sandwich

Thousands of world-famous rhododendrons in more than 100 varieties offer an explosion of spectacular blooms at the Rhododendron Festival at Heritage Museums & Gardens. Photograph yourself surrounded by walls of flowers, immerse yourself in the story of Heritage’s fascinating rhododendron legacy on a self-guided walking tour, learn proper plant care and pruning techniques at a hands-on garden discovery cart, and take home one of these signature plants from the special plant sale. There’s even a fun activity guide highlighting these amazing plants designed just for kids and families! Pre-purchase of admission tickets is recommended.

Clay Hansinger - Sharring Kindness

Clay Hansinger, clinical services manager, will represent CCHC at Sharing Kindness walk.

Sharing Kindness Suicide Awareness Walk

Saturday, May 16
Registration begins at 8:30 a.m.
Veterans Park Beach, Hyannis

The signature fundraiser for Sharing Kindness, the Suicide Awareness Walk is a three-mile (5K) loop walk that brings together community members to remember those who have died by suicide, support survivors of suicide loss and raise awareness of the stigmatized issues of brain health and suicide. Cape Cod Healthcare is proud to sponsor this meaningful event, which serves as an annual day of healing, storytelling and connection through shared experiences. 8:30 a.m.: Registration + pre-walk activities | 10 a.m.: Opening ceremony + walk begins.

Hyannis Open Streets

Sunday, May 17
Noon to 4 p.m.

Enjoy a car-free day in downtown Hyannis as Main Street transforms into a bustling pedestrian zone during the annual Open Streets event. Soak in the fresh spring air with live music, street performers, local vendors, outdoor dining and family-friendly fun. Whether you stroll, bike or dance your way through town, it’s a vibrant celebration of community spirit—free and open to all!

Hyannis HyArts Artist Shanties

May through October
Opens at 11 a.m. daily

Step into the vibrant world of Cape Cod creativity at the Hyannis HyArts Artist Shanties. Located just steps apart on Ocean Street and along Hyannis Harbor, these 12 seaside shanties feature local artists and artisans showcasing and selling their handmade work. Discover a wide variety of media including ceramics, mosaics, wood turning, fiber art, paintings, photography and jewelry. Meet the makers, watch them work and take home a unique piece of Cape Cod art.

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