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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!

Glassblower's Christmas Tree Unveiling & Members Appreciation Party

When: November 13, 2026, 5:00 p.m. to 7:00 p.m.

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

Admission:  Free

More Info: Glassblowers' Christmas Opening Event

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. This festive evening event is free and open to the public.

Museum members in attendance will receive a token of SGM's appreciation. So if you're not yet a member, this event would be the perfect time to join!

Brewster Ladies Library Annual Pottery Sale

When: November 2026 date - TBA

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

Admission: Free

More Info: Brewster Ladies Library

Eight very 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.

First Congregational Church of Falmouth Artisans Fair

When: November 2026 date - TBA

Where: First Congregational Church of Falmouth, 68 Main Street, Falmouth MA

Admission: Free

First Congregational Church's crafts fair features artisans and crafters that make glass & wood crafts, pottery, knitting & sewing, art work, jewelry, paper crafts, candles, photography, and so much more.

Revolutionary War Experience

When: November 2026 date - TBA

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.

Outermost Contra Dance

When: November 2026 date - TBA 

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

Admission: $15 general admission; $10 for those under 30; $5 with student ID

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!

Holidays at Highfield

When:  November 2026 dates - TBA

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

Admission: $15 for Members; $20 for Non-members; Children & Military are FREE

More Info: Holidays at Highfield

Highfield Hall is gearing up for another spectacular Holiday season featuring dazzling decorations, festive music and magical displays. And the Gift Gallery will once again be alive with artisan gifts for all ages.

*Twilight Fridays: New this year, special Friday evening hours from 4:30 – 6:00 p.m.  Admission for Twilight Fridays is $30 per adult. Libations & light snacks provided.

Pre-registration is encouraged. 

Seaside Holiday Fair

When: November 2026 date - TBA 

Where: Mashpee Congregational Church, 259 Shore Dr., New Seabury, Mashpee, MA

Admission: Free

More Info: Mashpee Congregational Church

All are invited to the festive Seaside Holiday Fair at MCC!

Gift shop in the Christmas boutique features beautiful handmade items, linens, scarves, crafts, vintage and estate jewelry and more!

Follow the red balloons to 259 Shore Dr., Mashpee, in the Popponesett Market Place in New Seabury.

Polar Express Christmas Train

When:  November 2026 dates - TBA

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!

Lighting of the Pilgrim Monument

When: November 25, 2026

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!

Holiday Open House at Nauset Model Railroad Club

When: November 2026 dates - TBA 

Where: Nauset Model Railroad Club, Hilltop Plaza, Orleans

Admission: Free

More Info: Nauset Model Railroad Club

The Nauset Model Railroad Club's Holiday Open House is a "don't-miss" for model railroad fans of all ages. Over 2,000 feet of display space features a variety of model trains chugging and tooting through miniature scenes festively decorated for the Holidays.

"Gardens Aglow" Opening Night

When: November 2026 dates - TBA   

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

Admission: 2026 ticket prices - TBA

More Info: Heritage Museums & Gardens

Heritage Museums & Gardens is putting on the glitz again this Holiday Season with it's treasured annual event - Gardens Aglow!

At this extra-special time of year, the good folks at Heritage adorn their acres of beautiful gardens and woodlands with more than 10 miles of twinkling, sparkling lights. It's truly an awesome thing to see!

Come stroll throughout the grounds and buildings where you'll enjoy festive holiday displays, family-friendly activities, marshmallow-roasting, music and special performances, visits with Santa Claus, displays of model trains - and even a visit by some baby animals.

'Tis the Season in Orleans

When: 2026 dates - TBA

Where: Various locations in Orleans

More Info: 'Tis the Season in Orleans

This popular town-wide celebration of the Holidays begins with the annual tree lighting on Friday evening. Join Santa and Mrs. Claus for breakfast on Saturday. And put on your running/walking shoes for the ever-popular Santa Stampede 5k and free Kids Fun Run.

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

Then head out for some great shopping and yummy food as the festivities continue all around the town!

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, artist 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!

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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