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Cape Cod Events
May 2020

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 for the fuzzy photo. We were trying to keep our distance and not float into the fray! ;-)

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

From the annual Cape Cod Maritime Days celebration to lighthouse tours, art gallery openings and the world-famous Figawi Regatta on Memorial Day weekend, there's a lot of fun stuff to see and do on Cape Cod in May!

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 2020

Cape Cod Maritime Days

When: May 1 - 31, 2020

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.

During Maritime Days on Cape Cod, events and special activities take place in nearly every town. Some highlights include harbor cruises, guided kayak tours, special museum and gallery exhibitions, a Maritime History Symposium, and much more.

Brewster In Bloom Festival

When: May 1, 2 & 3, 2020

Where: Various venues in the town of Brewster

Admission: Many events are free

More Info: Brewster in Bloom

The annual Brewster in Bloom Festival is a weekend-long extravaganza that includes an antiques and art excursion, a band concert, a 5K run, kids' events, sidewalk sales, free hayrides, arts & crafts shows, a music festival, all topped off with the Brewster in Bloom Parade on Sunday afternoon.

Visit the beautiful "Sea Captains Town" of Brewster and join in on the celebration!

Lighthouse Tours at Highland Light

When: Daily starting in mid-May (Thursday-Monday only, early May)

Where: Highland Light (more formally known as "Cape Cod Lighthouse"), North Truro

Admission: Adult $5; Youth and Senior $5

More Info: Highland Light; (508) 487-1121

At Highland Light, the oldest working lighthouse on the east coast, a winding staircase leads from the base to the lantern room. The view from the top is spectacular!

For anyone who's not able (or inclined) to climb the stairs, there's an interesting little museum and memorabilia area at the base that's well worth seeing.

Note: Click here to find more lighthouse tours on the Cape

Harbor Your Arts Artist Shanties - Opening Day

When: Opening Day is May 15, 2020 

Where: Hyannis Harbor/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.

Chatham Farmers Market

When: Tuesdays from 3:00-6:30 p.m. (Opening day 2020 - TBA)

Where: 1652 Main Street, Chatham (at Local Color Art Gallery and Ocean State Job Lot)

Admission: Free

More Info: Chatham Farmers Market - FB

This farmers market is filled to the brim with farm fare vendors. Just a few of their offerings: seasonal veggies and fruits; grass-fed beef, pork and lamb; free range chickens and turkeys; farm-fresh eggs; jams and jellies; baked goods; ginger beer and wine; flowers, herbs and herbal products; and local artists' works.

Rhododendron Festival

When: 2020 dates - TBA

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 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: May 22-25, 2020

Where: Hyannis / Nantucket

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. On Saturday morning, the large, colorful fleet gathers just outside Hyannis' inner harbor, waiting for the 10 a.m. start signal to begin their race to Nantucket.

If you'd like to see them off, you'll have good 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!