Although the world tends to think of Cape Cod as a summer playground, visitors are often surprised to discover that is a year-round vacation destination, offering something wonderful to fall in love with every month of the year. Even during the coldest months, visitors can help but find the romance in snow-covered beaches, roaring fires creating comfort and coziness as storms rage outside, and the fun that can be had attending special events while wearing their warmest and most colorful winter gear. And because attending these special events often gives travelers an authentic peek into the world of Cape Cod, we at New England Vacation Rentals have created this month by month guide to the most popular Cape Cod events occurring; coming home to the comfort and charm of our seasonal sanctuaries is just a bonus that the luckiest and most discerning of travelers can enjoy!

Looking for Cape Cod Vacation Cottages? Click Here!


The start of a new year is always an exciting thing. Our calendars are waiting to be filled with activities, events, and special occasions and on Cape Cod, it is a quiet month. The sunrise over the beaches comes much later giving us a better chance of enjoying them than in the summer months when we are still sleeping during those glorious moments and these events help start out the new year on the right foot.

FOYCA’s Annual Polar Bear Plunge, Smugglers Beach in South Yarmouth

We don’t quite understand the appeal, but the Polar Bear Plunge is an event scheduled for every January, during which participants take a dip in the frigid waters, paying $25 for the opportunity. The money does go to charity and the idea is to only submerge yourself and then get back out so it shouldn’t be that bad, if this is something that appeals to you.

S’mores & More at Long Pasture, Long Pasture Wildlife Sanctuary

Sponsored by MA Audubon’s Society, this event starts with a walk through the sanctuary looking and listening to the owls and other creatures of the night and finishes with a campfire, gooey and delicious s’mores, and an educational talk about the owls as the moon rises over the landscape. This event takes place on a Friday with a full moon.

Sunset over a beach


The shortest month of the year often seems like the longest one as winter has firmly dug in and the cold and snow seems to never stop, but there are still some events that will make your February vacation on Cape Cod shine bright.

Orleans Farmers Market, Saturdays from 10 AM Until Noon, 44 Main Street in Orleans

Surprise! Not all farmers markets on Cape Cod close down after the last of the summer tourists leave; some, like this one, simply move indoors! Offering a great opportunity to stock your pantry with fresh produce and homemade baked goods, it is also a great chance to get a peek at the renovated Old Firehouse, a structure originally finished in the 1920s.

Yarmouth Winter Carnival, Skull Island, 934 Route 28 in South Yarmouth

This fun event is sure to be an exciting adventure for travelers of all ages, celebrating the season of snow with food trucks, magic shows, petting shows, and an ice skating rink (synthetic) that will add a romantic Hallmark movie experience to your winter vacation on Cape Cod.

Beach at sunrise


Warmer days are within sight, and as spring begins to make itself known, we celebrate the season with these special events taking place on Cape Cod in March.

Cape Cod St. Patrick’s Day Parade, Route 28 from South Yarmouth to West Yarmouth

Everyone loves a parade, and no one celebrates St. Patrick’s Day like a group of people from Massachusetts and this one is Yarmouth is the perfect example. Offering colorful floats, marching bands, and beautiful people, your kids especially will like this parade when they catch the candy and treasures thrown into the crowds.

 Hyannis Marathon Weekend, Emerald Resort & Conference Center, 35 Scudder Lane in Hyannis

 Let’s keep this a secret between us, but the Marathon weekend is one we look forward to every year. Offering three days of fun events, including pasta dinner party, awards ceremonies, and the post-race party, it feels good getting outside again, and yes, we even love the 5K Fun Run, Marathon, Half Marathon, and Marathon Team Relay.

Grassy beach


April may be one of our favorite months on Cape Cod, as the sun shines longer, the air turns soft, and the flowers begin to poke through the dark earth as the snow melts away. April is also the month when one of our more unusual events takes place, one that is, of course, listed below.

Cape Cod Herring Runs, Brewster, Bourne, Mashpee, Sandwich, Harwich, and More Towns and Villages Throughout the Cape

The Herring Runs are the unusual event we spoke about above, and yes, we gather at the places listed above to watch the annual migration of the river herring heading from the ocean to fresh waters preparing to spawn. Running for miles, surviving the dangers of the hazards they pass along the way. What makes this so cool is the sheer numbers of silvery fish swimming through the waters of the estuaries and climbing the fish ladders humans have created to help them with their journey.

Sandwich Bazaar, Wednesdays and Sundays April Through October, 34 Quaker Meetinghouse Road in Sandwich

This fun bazaar, also known as the Sandwich Flea Market, is the oldest and largest flea market on Cape Cod, making an appearance every April for 17+ years. Featuring an exciting array of merchandise that can range from local produce to organic treats for your favorite fur baby, the Sandwich Bazaar is worth planning a trip to Cape Cod to explore.

Sandy beach with bench


Memorial Day weekend is the start of our busy tourist season, but the entire month is when Cape Cod truly comes alive, with a variety of events inviting visitors to travel to our shores and explore authentic Cape Cod experiences.

Brewster in Bloom, Various Venues Throughout Brewster

April showers are supposed to bring May flowers, and we are eager to celebrate every bloom in Brewster with this super aromatic event. Offering a variety of events, including a Brewster in Bloom town parade, there will be merchandize for sale, a spring concert, even a Cape Cod 5 Bloom Run to look forward to in this festival that has taken place for over 30 years.

Celebrate Mom, Snow’s Home & Garden, 22 Main Street in Orleans

Snow’s Home & Garden shop has been a Cape Cod favorite for over 130 years, and their Mother’s Day event, Celebrate mom! is something we never want to miss. Offering raffles, giveaways, and gifts for the mom in your life, this event and shopping experience will make you wish you could Cape Cod your home.

Memorial Day Parades Across Cape Cod

In a world where parades are rapidly becoming a thing of the past, we hold on to the tradition with both hands, holding parades whenever possible and on Memorial Day can you think of a better way to honor our fallen heroes? Centerville, Dennis, Falmouth, & Yarmouth are where you should be when the next Memorial Day weekend rolls around.

Bird in flowers


Cape Cod is really hopping in June and the list of events that are taking place in June is so long, we aren’t going to waste your time with long descriptions, the events are all listed below.

Yarmouth Sand Sculpture Trail, Various Venues, All Month Long

If you have ever felt frustrated at your attempts to build sandcastles, the Yarmouth Sand Sculpture Trail isn’t going to make you feel any better about your skills, but it will fill you with awe as you explore the approximately 30 masterpieces created by the most talented sand sculptor on Cape Cod, Sean Fitzpatrick and on display all over Yarmouth.

Cape Cod Pirate Festival, 668 Route 28, the Old Yarmouth Drive-In West Yarmouth

Held on a variety of days in the month of June, this celebration of everything pirate is certain to be one of your favorite Cape Cod adventures. Theme days, costume contests, food, and grog are just a few of the things you can expect from the Cape Cod Pirate Festival.

Sand castle on beach


Fireworks on Cape Cod

July 4th is a holiday that is near and dear to our hearts especially as we are so close to where our country’s first steps towards independence began and most of Cape Cod will be celebrating this special holiday with fireworks and parades. Sandwich, Orleans, Chatham, Hyannis—whichever New England Vacation Rentals vacation escape you are staying in, there is sure to be a display not far away. The Hyannis Harbor Boat Parade is one event you should not skip in case you were wondering.

Barnstable County Fair, Cape Cod Fairgrounds, Route 151 in East Falmouth

The Barnstable County Fair has been around for more than a few moments, having entertained us for over 170 years. Offering all the rides, games, and fair food you dream about during the months the fair isn’t open, this activity will be loved by the entire family.

Fireworks on a beach


Summer’s end brings a mixture of sadness and joy to the residents of Cape Cod, as visitors who have become friends leave to begin to return home to their real lives, but the joy comes from shorter lines at the restaurants, so we make do. But before you leave, be sure to check out these fun events.

Hookers Ball, Chatham VFW, 150 George Ryder Road in Chatham

Relax. The Hookers Ball is NOT what it sounds like, we promise. This celebration of fresh from the boat seafood involves a fancy dinner (seafood, of course) live and silent auctions, and a variety of gifts, artwork, and services that can be bid on at the silent auction.

Colonial Day at the Manse, Josiah Dennis Manse, 61 Whig Street in Dennis Village

This journey back into the 1700s promises to be as fun and interesting as it is educational. The tour of the Manse Museum and Schoolhouse features costumed docents and a variety of townspeople performing everyday tasks in the same ways they would have been completed back in the early days of our country.

Dock with small buildings


In most years, September is when Labor Day takes place and Cape Cod grows quieter and more relaxed, but not before one last blast, as listed below.

Fireworks, Bonfires, and Holiday Parades

We celebrate Labor Day Weekend in big ways, and depending on which of our New England Vacation Rentals escapes you have chosen to make your own, there is sure to be a celebration of Labor Day taking place nearby. Fireworks Displays in Hyannis Harbor and West Dennis Beach, Beach Parties in West Dennis, and Craft Festivals in South Yarmouth are just a few events you can expect during your Labor Day adventures on Cape Cod.

Eastham Windmill Weekend, Windmill Green, and Other Places in Eastham

Talent shows, car shows, art shows, and lighthouse tours are some of the adventures you can expect to enjoy during the Eastham Windmill Weekend.

Red and white lighthouse


You won’t be able to keep from falling in love with fall during your October stay on Cape Cod,  especially as you take part in the events listed below.

  • Cranberry Harvest Season, Multiple Venues in Yarmouth, Sandwich, & Harwich – You’ve seen the commercials, now it is time to experience the reality while watching cranberry farmers harvest the cranberries in the bogs that can be found all over Cape Cod.
  • Fall Frolic & Pumpkin Patch, Chatham Bars Inn Farm, 3034 Main Street in Brewster – Everything fall is celebrated in the Fall Frolic & Pumpkin Patch, offering hot apple cider, live music, pumpkins, and pie contests.


We are thankful for our guests who visit all through the year and we are also thankful for these exciting events.

  • Gingerbread Lane & Artist Shanties, Hyannis Village Green in Hyannis – Christmas is right around the corner and if you aren’t shopping for gifts at Gingerbread Lane & Artist Shanties, what are you doing? This annual event is one of our favorite ways to find gifts to put under the tree for the people we love best.
  •  Winterfest in Orleans, Various Locations in Orleans – Celebrating the biggest holiday of the year, Winterfest in Orleans offers a visit from Santa, candlelight stroll with Mrs. Claus, and a tree lighting ceremony, preparing guests for everything that is wonderful about Christmas.

Person drinking hot cocoa


 And just like that, the year is over, except for these last December events.

  • Harwich for the Holidays, Various Locations in Harwich – Santa arriving by firetruck, open houses by local shops, and tree lightings in the villages of Harwich are all a part of the Christmas celebrations in Harwich.
  •  Hyannis Village Christmas Stroll, Main Street and Hyannis Harbor in Hyannis – Music, food, shopping, and Santa make this annual event one of our favorites, but it is the boat parade that will ensure you never forget this Christmas event.

Find Chatham Holiday Rentals Here!

Come Home to New England Vacation Rentals

 Every event will be your favorite when you come home to our exciting and comfortable Cape Cod escapes at the end of every day of your vacation. Reserve your favorite today!