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Cape Cod Events
May 2021

Updated: March 5, 2021

When the calendar turns to May, the Cape Cod events schedule heats up ... just like our weather!

Start of the annual Figawi yacht race in HyannisPre-start of the Figawi Sailboat Race from Hyannis to Nantucket. (Sorry to say, the Figawi has been postponed again to 2022.)

Events throughout the month of May have us all outdoors enjoying the spring sunshine and the first balmy beach days of the season. 

Cape Cod Events Each Month

January | February | March | April | May | June | July
August | September | October | November | December

Here's what's going on around the Cape this month: 

Fairs, Festivals & Special Events on Cape Cod
May 2021

Cape Cod Maritime Days

When: May 1 - 31, 2021

Where: Towns and venues all across Cape Cod

Admission: Many events free

The annual Maritime Days festival heralds summer by the sea with a month-long celebration dedicated to our rich seafaring heritage.

This year's Maritime Days events have yet to be determined. In past years, they've included harbor cruises, guided kayak tours, special museum and gallery exhibitions, a Maritime History Symposium, and much more.

Brewster In Bloom Festival

When: April 30, May 1 & 2, 2021

Where: Various venues in the town of Brewster

Admission: Free

More Info: Brewster in Bloom

The annual Brewster in Bloom Festival is a weekend-long celebration of spring in the town of Brewster.

This year, the annual Fine Arts & Crafts Show has gone virtual, as has the popular Brewster Band Concert.

In-person events and activities encourages everyone to get out and explore the town. Discover Brewster's rich history and scenic spots with a self-guided Cultural Trail tour. Come see all the festive decorations adorning the homes entered in the Brewster in Bloom Lawn Display Contest. 

As it has for the past 30+ years, Brewster in Bloom will have something for everyone to enjoy in 2021!

Harbor Your Arts Artist Shanties - Opening Day

When: Opening Day is May 21, 2021 

Where: Hyannis Harbor Overlook and Bismore Park, Ocean Street, Hyannis

Admission: Free

More Info: HyArts Art Shanties

These adorable "shanties" house artists and artisans whose works include ceramics, painting, jewelry and more. Items are for sale at very reasonable prices (IMHO). And even if you're not in shopping mode, it's a pleasure peeking at the artists' creations as you stroll along the harborfront.

The shanties are open on weekends only from opening day in May until mid-June, then every day through late September.

Rhododendron Festival

When: May 21-30, 2021

Where: Heritage Museums & Gardens, Sandwich

Admission: $20/adult; $10/youth (3-11); Members and children 2 and under Free

More Info:  Heritage Museums & Gardens

This is one of the Cape Cod events I look most forward to each spring. The grounds at Heritage are a breathtaking sight to behold with thousands of Rhododendrons in bloom from late May into early June!

Plan to spend a few hours or more here, exploring the acres of gardens, miles of walking trails, and the museums filled with art, American history, and antique autos. The kids will love riding on the carousel!

Figawi Race Weekend

When: Memorial Day Weekend, 2021

Where: Hyannisport / Nantucket Sound

Admission: No admission fee for spectators

More Info:  Figawi Race Weekend

The annual "Figawi" Regatta is recognized as one of the premier yacht regattas on the east coast. For this year's 50th annual Figawi Regatta, the teams will race on Saturday and on Sunday from a starting point at Hyannisport Jetty on a course around Nantucket Sound.

Start time is 10 a.m. If you'd like to see them off, you'll have a good vantage point from Kalmus Beach, Orrin Keyes Beach, or Sea Street Beach in Hyannis. (See my Hyannis beaches page for directions, parking info, etc.)

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Related Pages:

Lots More Fun Things to See & Do on Cape Cod


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Important Note: The date, time, place, admission charges, etc. of the events on this page may be changed by the event sponsor at any time, without my knowledge. Please be sure to confirm all information directly with the sponsor before you make any plans!