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Cape Cod Events
November 2026 

Pilgrim Monument at the Holidays

*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
November 2026

Provincetown Food & Wine Festival

When: November 5 - 8, 2026

Where: Various venues in Provincetown

Admission: Varies by event

More Info: Provincetown Food & Wine Festival

This popular event is Provincetown's ultimate showcase of exceptional foods and wines. 

Festival activities include wine dinners, wine tastings, live performances, the GRAND Tasting, and much more.

No doubt this year's Provincetown Food & Wine Festival will once again delight all foodies and wine lovers!

Daniel Roth in Concert

When: November 6, 2026, 7:30 p.m.

Where: Church of the Transfiguration, 9 Bay View Drive, Orleans MA

Admission: $40 general; $35 seniors; free for students and youth 18 and under

More Info: Daniel Roth in Concert

Internationally acclaimed organist Daniel Roth returns to Cape Cod for an evening of Bach, Franck and Widor on the Church of the Transfiguration's St. Cecilia Organ.

Roth served for decades as Titular Organist at St. Sulpice in Paris and is known internationally as both a performer and improviser.

The Church's surround-sound organ, built with restored pipework from twelve historic E.M. Skinner organs, makes this a particularly unique setting to hear him perform.

Arts Empowering Life Programs

When: November 7 & 21, 2026, 3:30 to 4:30 p.m.

Where: Brewster Performing Arts Center, 95 Southern Eagle Cartway, Brewster MA

Admission: Free

More Info: Arts Empowering Life

Arts Empowering Life brings two very different free programs to its Brewster Performing Arts Center this month.

In Lost Voices of Byzantium (November 7), chanter and scholar Spyridon Antonopoulos explores medieval Byzantine chant and the work behind reconstructing music from centuries-old sources. Arts Empowering Life

In Mastering the Craft: the Gig, the Gear, the Goals (November 21), percussionist and educator Damon Grant combines performance and conversation in a look at the tools, experience and choices that go into building a life as a working drummer.

Revolutionary War Experience

When: November 8, 2026, noon to 4 p.m.

Where: Brewster Windmill Village, 51 Drummer Boy Road, Brewster MA

Admission: Free

More Info: Brewster Historical Society

Come watch Brewster Colonial Artillery Company's members - all in period dress - as they drill with “Alice,” the Unit’s muzzle-loading cannon, and demonstrate manual arms and firing the muzzle-loading musket known as “Brown Bess.”

There'll also be lessons in writing with a quill pen, playing trap ball (a sort of colonial baseball with a twist!), and opportunities to speak with militia members about colonial life, the Cape’s role in the Revolution, and the resulting Republic’s evolution as a Nation State.

Weather permitting, there will be tents, a bell of arms set up, and the possibility of cooking demonstrations, too.

Glassblowers' Christmas 

When: November 13 - December 30, 2026

Where: Sandwich Glass Museum, 129 Main Street, Sandwich MA

Admission: Free to visit the Gift Shop and Glassblowers’ Christmas display. (Museum admission not included.)

More Info: Glassblowers' Christmas

It’s the most wonderful time of the year at Sandwich Glass Museum!

As the year draws to a close, the museum will be celebrating the holidays in style with Christmas tree ornaments and other winter decor to beautify your home.

Come admire the freshly decorated trees in this kick-off to the holiday season.

*Note: The Museum will be closed Thanksgiving Day.

Brewster Ladies Library Annual Pottery Sale

When: November 14 - 28, 2026 during museum open hours

Where: Brewster Ladies Library, 1822 Main St., Brewster, MA

Admission: Free

More Info: Brewster Ladies Library Pottery Sale

At this popular event, talented local Cape Cod potters present their work for the Annual Holiday Pottery Show & Sale.

An array of handmade sculpture, mugs, bowls and various items will be available with a portion of the proceeds going directly to the Ladies Library.

Holidays at Highfield

When:  November 19–22 & 27–29, 2026, 10 a.m. to 4 p.m.; Twilight Hours November 20 & 27, 4:30 to 6 p.m.

Where: Highfield Hall & Gardens, 56 Highfield Drive, Falmouth, MA

Admission: $20 members; $25 non-members; children under 17 and military free. (Twilight Hours: $35 per adult includes libations and light snacks.)

More Info: Holidays at Highfield

This year’s Holidays at Highfield takes visitors back to Christmas in the Gilded Age with ’Twas the Night Before Christmas: Life Above & Below Stairs.

See how the Beebe family prepared for Christmas “above stairs” while servants worked behind the scenes “below stairs” to get the mansion ready for the festivities.

The popular Gift Gallery returns with handcrafted artisan gifts, along with a holiday craft room for children and families.

*Note: Highfield is also offering two special guided tours: The Servants’ Tour on November 22nd and The Designers’ Tour on November 29th. Both include access to parts of the holiday exhibition not available during regular visits. Tours begin at 9 a.m.; tickets are $40–$45, with advance registration required.

Outermost Contra Dance

When: November 20, 2026; doors open at 6:15 p.m.; Contra Basics Workshop at 6:30 p.m.; dancing begins at 7 p.m.  

Where: Wellfleet Preservation Hall, 335 Main Street, Wellfleet MA

Admission: $15 regular admission; $10 for ages 30 and younger; $5 with student ID. Pay at the door.

More Info: Outermost Contra Dance

Put on your dancin' shoes for this fun event at Preservation Hall!

Contra dancing is the older cousin to the square dance. No fancy footwork is needed – if you can walk, you can contra dance!

All the dances are taught and called. If you're new to contra dance, join the free "Contra Basics Workshop" at 6:30 p.m. to learn the basic moves. (No need to bring a partner; there are plenty of friendly people in this welcoming dance community.)

Come to dance or come just to listen. All are welcome!

Polar Express Christmas Train

When:  November 20, 2026 is opening day; multiple trips throughout the month

Where: Buzzards Bay Depot, 70 Main Street, Buzzards Bay

Tickets: Prices vary by trip date/time and seating class  

More Info: Cape Cod Central Railroad

The delightful children's story, The Polar Express, comes alive as you board Cape Cod Central Railroad's  festively decorated train cars for a ride to "the North Pole". 

As the Christmas train chugs along the tracks, everyone gets into the Holiday spirit with merry music, a reading of The Polar Express story, sweet treats, and mugs of hot cocoa.

Of course, the Jolly Old gentleman himself will be there when the train stops just outside the North Pole, greeting everyone with a rousing "Ho, Ho, Ho!".

What a fun way for the whole family to kick off the Holiday Season!

Eastham Turnip Festival

When: November 21, 2026

Where: Various locations in Eastham

Admission: Many activities are free

More Info: Eastham Turnip Festival

Come celebrate the humble Eastham turnip at one of Cape Cod's quirkiest annual festivals!

Turn Up for Fun Day at Eastham Public Library brings free turnip-themed entertainment and amusements from 10 a.m. to 3 p.m. There'll also be live music at Chapel in the Pines, with the Cape Cod Ukulele Club at 11 a.m. and Watch Your Step at 1 p.m.

And come hungry! Local restaurants will get into the act for Taste of Turnip Day, offering everything from turnip soups and side dishes to entrées and desserts featuring Eastham's famously sweet local turnips.

*Note: More 2026 festival activities to be announced soon.

Lighting of the Pilgrim Monument

When: November 25, 2026, 3:00 to 5:15 p.m.

Where: High Pole Hill, Provincetown

Admission: No charge to watch the illumination

More Info: Pilgrim Monument Lighting

The spectacular 252-foot tall Pilgrim Monument dazzles the night sky with thousands of white lights, celebrating the Pilgrims’ First Landing in Provincetown in November 1620.

The lights continue to shine through the first week of January. It's a beautiful sight to see!

Chatham Turkey Trot

When: November 26, 2026, 8 a.m.

Where: Oyster Pond Parking Lot, 80 Stage Harbor Road, Chatham MA

Entry fee: $35 through November 6; $45 November 7–26. Registration required.

More Info: Chatham Turkey Trot

Start Thanksgiving Day with a little fresh air and exercise at this family-friendly 5K run/walk through Chatham.

Runners and walkers of all ages are welcome, and baby joggers/strollers can come along, too.

Proceeds from the Turkey Trot benefit the Lower Cape Outreach Council, which provides food and emergency financial assistance to people in need across the Lower and Outer Cape.

The Canteen Holiday Market

When: Opening weekend November 27–29, 2026, 11 a.m. to 5 p.m.; additional dates through December.

Where: The Canteen, 225 Commercial Street, Provincetown MA

Admission: Free

More Info: The Canteen Holiday Market

This isn't your typical Holiday craft fair! Each year, The Canteen transforms its backyard into a festive little holiday village filled with local makers, good food and drinks, and plenty of Holiday cheer.

Browse handcrafted goods from local artisans, then warm up with something tasty from the Backyard Bar, Bakeshop or Food Hut.

The Holiday Market also hosts special happenings throughout the season, making this as much a place to hang out and enjoy the festivities as it is a place to shop.

"Gardens Aglow" Opening Weekend

When:  November 27–29, 2026, 4:30 to 8:30 p.m.   

Where: Heritage Museums and Gardens, 67 Grove Street, Sandwich

Admission: Advance timed tickets: $30 adults; $20 ages 3–17; free for ages 2 and under. Member discounts available.

More Info: Gardens Aglow

Heritage Museums & Gardens is putting on the glitz again this Holiday Season with its treasured annual event, Gardens Aglow!

At this extra-special time of year, the good folks at Heritage fill their beautiful gardens and woodlands with dazzling light displays and festive decorations. It's truly an awesome thing to see!

Come stroll throughout the grounds and buildings where you'll find lighted tunnels, a reindeer scavenger hunt, marshmallow-roasting, visits with Santa, a model train display, seasonal treats, rides on the 1908 Looff carousel, and plenty more holiday fun.

*Note: Tickets for this event go on sale to the general public on October 21st at 8 a.m., and they sell out very quickly. 

"Spectacle of Trees" Opening Weekend

When: November 27-28, 2026, from 10 a.m. to 5 p.m.

Where: JFK Hyannis Museum, 397 Main Street, Hyannis MA

Raffle: $10 per chance to win a tree and all its prizes

More Info: Spectacle of Trees

The fabulous "Spectacle of Trees" is back at the JFK Hyannis Museum!

Local nonprofit organizations decorate Christmas trees, then load them up with all kinds of amazing gifts. We're talking gift cards, artwork, electronics, event tickets, vacation packages, and lots of other goodies.

Here's the fun part: For a $10 donation, you get a "Tree Bucks" raffle ticket to enter the drawing for whichever tree catches your fancy. And if your name is drawn, you win the beautifully decorated tree and all the gifts that come with it!

Even if you don't win, your donation helps support the local nonprofit whose tree you chose. How's that for a wonderful win-win holiday tradition?!

Holiday Open House at Nauset Model Railroad Club

When: November 28, 2026, from 1-4 p.m.  

Where: Nauset Model Railroad Club, Hilltop Plaza, Orleans

Admission: Free

More Info: Nauset Model Railroad Club

This is opening day for Nauset Model Railroad Club's Holiday Open House. 

Come see over 2,000 feet of display space featuring a variety of model trains chugging and tooting through miniature scenes festively decorated for the Holidays.

This popular annual event is a "don't-miss" for model railroad fans of all ages!

Lighting of the Lobster Pot Tree

When:  November 28, 2026, 5:00 - 6:00 p.m.   

Where: Lopes Square in Provincetown

Admission: Free

More Info: Lobster Pot Christmas Tree - FB Page

Made from 100+ lobster pots stacked over 2 stories high and decorated with ribbons, garland and thousands of festive lights, Provincetown's beloved lobster pot Christmas tree will put you in the Holiday mood for sure!

The tree is first illuminated in late November and stays lit every night through the Holidays. So there's plenty of time for you to come see it!

'Tis the Season in Orleans

When: November 28 - December 5, 2026

Where: Various locations in Orleans

More Info: 'Tis the Season in Orleans

This popular town-wide celebration of the Holidays includes the annual tree lighting, breakfast with Santa and Mrs. Claus, the  ever-popular Santa Stampede 5k, and a special Holiday edition of First Friday.

Throughout the week, don't miss the great shopping and yummy food all around town!

Holiday Strolls, Tree Lightings & Caroling

When: From late November through mid-December

Where: Towns and villages across Cape Cod

Admission: Free

When Thanksgiving Day is in the rear-view mirror, it's time for our annual Christmas Strolls, tree lightings on the village green, community caroling, and Santa's arrival by boat or fire truck.

These beloved Holiday events are sure to get you into the Spirit of the Season!

>>See: Christmas Strolls, Tree Lightings, Caroling & More 

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