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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. Here's just a small sampling of what's happening:

• Enjoy the ever-popular Brewster Band's Spring Concert.
• Check out all the wares for sale at the open-air Fine Arts & Crafts Show.  
  
• 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!

Parker's River Landing - Grand Opening

When: May 2, 2026, 10 a.m. to 3 p.m.

Where: Parker's River Landing, 669 Rt. 28, West Yarmouth MA

Admission: Free

More Info: Parker's River Landing Grand Opening

Celebrate the grand opening of Parker’s River Landing, a newly transformed waterfront space built with coastal resilience in mind.

The former drive-in site now features an elevated boardwalk, playground, restored habitats, and a kayak launch designed for changing coastal conditions.

A Coastal Resiliency Fair will bring in local experts and hands-on exhibits focused on protecting the shoreline and adapting to climate change. The day also includes a ribbon cutting, guided tours, and plenty of family-friendly activities like a kids’ zone, touch-a-truck, food trucks, and vendors.

*Note: Parking on site is limited. Additional parking and a shuttle will be available from Seagull Beach.

Rhododendron Festival

When:  May 15 - 23, 2026, 10 a.m. to 5 p.m.

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

Admission: $26/adult; $16/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!

Annual Rowing Rendezvous

When: May 16, 2026, 10 a.m. to 2 p.m.

Where: Kalmus Beach, Hyannis MA

Admission: Free

More Info: Annual Rowing Rendezvous

Come celebrate traditional rowing on Cape Cod with boats on the beach, rowing demonstrations, and hands-on opportunities to try a variety of New England–style traditional small boats.

Members of the Cape Cod Traditional Small Craft Association will be bringing their own boats — many of them built by the rowers themselves — and making them available for short rows.

New to rowing? No problem! Assistance will be available for beginners. You will get your feet wet, so plan accordingly!

Hyannis Open Streets

When: May 17, 2026, noon to 4 p.m. (rain date May 31) 

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.

"Bee Happy" Luncheon

When: May 21, 2026, 11 a.m. to 1 p.m.

Where: Mills River Rescue & Sanctuary, 240 River Road, Marstons Mills MA

Admission: $20/person (reservations required)

More Info: Bee Happy Luncheon

Come join Patti and her dedicated team of volunteers at Mills River Rescue and Sanctuary for their "Bee Happy" Luncheon.

This is your family's chance to visit with the adorable ponies, donkeys, bunnies, ducks and other animals that are so fortunate to have found a home at Mills River Rescue & Sanctuary.

Guests at this special event will enjoy a light lunch, fun games with prizes, and a special pony presentation.

This is sure to be a great time for a great cause!   

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.)

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!