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Cape Cod Events
May 2026

Pre-start of the Figawi Sailboat Race in Hyannis

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

*Note: Most events go ahead as planned. Even so, weather or other unforeseen factors occasionally lead to postponements or cancellations. So it's always best to double-check with the organizer (see links below) before you head out.

Fairs, Festivals & Special Events on Cape Cod
May 2026

Cape Cod Herring Runs

When: Through mid-May during daylight hours

Where: Multiple locations around the Cape

Admission: Free

More Info: Herring Runs on Cape Cod

Herring? The fish? Running??? Yes, indeed! And they climb ladders, too! ;-)

We see these amazing feats every spring as thousands of herring migrate from the wide-open ocean to our local rivers, streams, lakes and ponds to spawn.

Where are the best places on the Cape to watch herring running and climbing? Click here to find out!

Museum Mondays in May

When: Mondays in May 2026

Where: Multiple museums across Cape Cod

Admission: Free

More Info: Museum Mondays in May

During the month of May, several of Cape Cod's top museums will be open for FREE on Mondays as part of "Museum Mondays in May".

Whether you're an art lover, history buff, or simply looking to have some fun, this is a perfect opportunity to enjoy some of the best cultural venues on the Cape without having to spend a penny on admission.

Northeast Regional Parrot Head Convention

When: April 30 - May 3, 2026

Where: Margaritaville Resort Cape Cod, 1225 Iyannough Road, Hyannis MA

Admission: General admission for the convention is $125 per person for the entire weekend; $225 VIP admission comes with lots of extra perks

More Info: Parrot Head Convention

Parrot Heads, it’s time to party with a purpose!

Join fellow Parrot Heads at Margaritaville Resort Cape Cod for a three-day tropical celebration filled with live music, island vibes, games, vendors, and non-stop fun.

• Live Trop Rock music
• Parrot head games & themed parties
• Meet Parrot Heads from across the country
• Support local charities while having a blast!

Brewster In Bloom Festival

When: May 1 - 3, 2026

Where: Various venues in the town of Brewster

Admission: Free

More Info: Brewster in Bloom

The annual "Brewster in Bloom Festival" celebrates spring in the town of Brewster.

Events during the festival encourage everyone to get out and explore all around the town:

• Discover Brewster's rich history and scenic spots with a self-guided Cultural Trail tour.
  
• Check out all the wares for sale at the open-air Fine Arts & Crafts Show at Drummer Boy Park.
  
• Enjoy the ever-popular Brewster Band's Spring Concert.
  
• Join in on the "Cape Cod 5 Bloom Run".
  
• And be sure not to miss the Brewster in Bloom Town Parade!

As it has for many decades, the Brewster in Bloom Festival will have fun for all in 2026!

Touch-a-Truck

When: May 2026 date - TBA

Where: Wellfleet Drive-In Theater, 51 US-6, Wellfleet, MA

Admission: Free

More Info: Wellfleet Police Dept. FB Page

Touch-A-Truck comes to us courtesy of the Wellfleet Police Association, the Eastham Police Union and Wellfleet Drive-In.

What kind of vehicles will be there? Police cars, fire trucks, construction trucks, emergency vehicles and more! 

So put this much-loved annual event on your calendar, and plan on a fun day with the family!

Rhododendron Festival

When:  May 2026 dates - TBA

Where: Heritage Museums & Gardens, 67 Grove Street, Sandwich MA

Admission: $25/adult; $15/youth (3-17); Members and children 2 and under Free

More Info:  Rhododendron Festival at Heritage

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!

Harbor Your Arts Artist Shanties: Opening Day

When: May 15, 2026 at 11 a.m.

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.

Master Gardeners' Annual Plant Sale

When: May 16, 2026, 8 a.m. to noon (or until plants sold out)

Where: Cape Cod Fairgrounds - The Marketplace Barn - West Gate, Route 151 & Currier Road, East Falmouth, MA

Admission: Free

More Info: Master Gardeners Association of Cape Cod

Looking for some amazing plants to add to your yard, garden or patio planters? The Master Gardeners have you covered with lovingly grown plants from their own greenhouses, gardens and local nurseries.

You'll find: native plants, hydrangeas, rhododendrons, perennials, dahlias, and succulents ... plus 50 tomato varieties, a fantastic selection of veggies, over 100 varieties of culinary and pollinator herbs, and more!

Proceeds from this popular annual event support the Master Gardeners Association of Cape Cod's scholarship fund and community programs including the children's garden, backyard horticulture, and the horticultural hot line.

Admission is free; and there's plenty of free on-site parking available, too.

Do plan to get there early. This sale draws a big crowd!

Hyannis Open Streets

When: May 2026 date - TBA 

Where: Main Street, Hyannis, MA

Admission: Free

More Info: Hyannis Open Streets

Remember when you were a little kid and your parents told you not to play in the street?

Today, everyone is encouraged to come to Hyannis to walk, dance, socialize, and yes ... play in the street!

This popular event is filled with family friendly games, live music, giveaways, performances by "Trevor The Juggler" and much more.

*Note: Main Street will be closed to vehicle traffic between Barnstable Road and Sea Street.

Figawi Race Weekend

When: Memorial Day Weekend, May 22 - 25, 2026

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 US east coast.

The warning signal sounds for the start of the race from Hyannisport to Nantucket on Saturday morning at 9:55 a.m.

To see the yachts gathering and watch them head off to Nantucket, you'll have a good vantage point from Kalmus Beach, Orrin Keyes Beach, or Sea Street Beach. (See my Hyannis beaches page for directions, parking info, etc.)

"Troops in the Spotlight"

When: May 2026 date - TBA

Where: Behind the Cape Cod Mall, Hyannis MA

Admission: Free 

More Info: Cape Cod Cares for Our Troops

Cape Cod Cares for Our Troops honors our country's fallen heroes - and all members of the military - with its annual "Troops in the Spotlight" event.

Come see the display of military vehicles and equipment. Show your support for our deployed troops. And most importantly of all, meet and greet members of our country's military and thank them for their service!

*Please consider making a monetary donation or donating a care package item to Cape Cod Cares for Our Troops. 

Wellfleet Restaurant Week

When: May 27 – June 2, 2026

Where: Multiple restaurants in Wellfleet

Admission: No tickets required

More Info: Wellfleet Restaurant Week

​Restaurant Week is a ​week-long event ​that gives both locals and visitors alike an opportunity to delight in all that Wellfleet has to offer before the kicking off the busy summer season.

There are no tickets or passes required for ​Wellfleet Restaurant Week.​ Simply dine out ​or shop ​at a participating restaurant​ or business and ​e​njoy special menu​ items and offerings​​.

This is the perfect time to Eat, Shop and Stay in Wellfleet, without the long lines and the fuss.

Related Pages:

Lots More 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!