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Cape Cod Events Calendar
October 2026

Watching the Cranberry Harvest on a Beautiful October Day

*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
October 2026

Cranberry Harvests

When: Throughout the month of October 2026

Where: Multiple cranberry bogs on Cape Cod

Admission: Free to watch on your own; costs vary for guided tours

More Info: See link below.

October is cranberry harvest time on Cape Cod!

If you've never seen acres of crimson berries floating on our local bogs, now's your chance to get out and watch our hard-working Cape Cod cranberry growers bringing in their crops.

It's a fascinating thing to see, and the photo opps are spectacular! 

* Read about: When & Where to See the Harvest

Pick Your Own Apples & Pumpkins

When: Throughout October 2026; picking dates vary

Where: Several farms on the Upper Cape

Admission: Varies by farm

More Info: See farm links below

Looking for a little hands-on fall fun? October is prime time for picking apples and pumpkins on Cape Cod.

Grab a bag, wear shoes you don’t mind getting a little dirty, and see what’s ready for picking at Crow Farm in Sandwich, or Tony Andrews Farm and Coonamessett Farm in Falmouth. Depending on when you go, you may find apples, pumpkins, or both.

*Note: Open days and times, and what’s available for picking, can change as the month goes along. So be sure to check with the farm before you head out.

Lighthouse Tours

When: Throughout October, 2026

Where: Multiple lighthouses across Cape Cod

Admission: Varies by lighthouse; some are free

More Info: Cape Cod Lighthouses

Lighthouse touring season isn’t over yet!

Several Cape Cod lighthouses are still open for interior tours in October, giving you a chance to climb the tower, check out the view from the top, and learn a little about the history of these old coastal beacons.

Tour days and hours vary by lighthouse, so check the link above to see which ones are open when.

Wellfleet Ghost Tours

When: Mondays & Thursdays in October 2026, 8 p.m.

Where: Wellfleet Historical Society & Museum, 262 Main Street, Wellfleet MA

Admission: $20 per person; advance reservations recommended

More Info: Wellfleet Ghost Tours

Is Wellfleet haunted? Here’s your chance to decide for yourself!

By lantern light, you’ll walk through the village to places where ghostly encounters have been reported and hear stories of Wellfleet hauntings past and present.

The tour lasts about an hour and covers less than a mile, with some uneven ground along the way. Space is limited, so book ahead if you want to spend an October night searching for Wellfleet’s resident spirits.

Love Farms Harvest Festival Series

When: October 3, 10, 17 & 24, 2026, 10 a.m. to 1 p.m.; live music until 4 p.m.

Where: Love Farms, 607 Main Street, West Dennis MA

Admission: Varies by event

More Info: Love Farms Harvest Festival Series

Love Farms celebrates the fall harvest on Saturdays through  October 24th, with different themes: Pickle Week, Oyster Week, Cranberry Week and Oktoberfest.

Each festival includes tastings, farm tours, hands-on activities and local vendors, with live music on the lawn afterward.

The weekly themes bring their own extras, too, from shell painting and cranberry garland-making to pumpkin painting and  Oktoberfest fun.

Pick your favorite Saturday, or come back for more than one!

Arts Empowering Life Concerts

When: October 2, 3, 9, 10, 17, 18 & 24, 2026; times vary by performance

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

Admission: Ticket prices vary by performance; free for students and youth 18 and under

More Info: Arts Empowering Life

Arts Empowering Life brings a varied lineup of concerts to its Brewster Performing Arts Center this month.

Wind Ensemble America 250: Pursuit of Happiness (October 2 & 3) celebrates American music with works by John Williams, Rodgers & Hammerstein, Leonard Bernstein and others.

Reflections: The Waters of Life with Chara Percussion (October 9 & 10) explores the many moods of water through music by Ravel, Debussy, Philip Glass and contemporary composers.

Creare Symphonia in Concert (October 17 & 18) features Vaughan Williams’ The Lark Ascending along with Finzi’s music for Shakespeare’s Love’s Labours Lost.

Then Grammy-winning Sō Percussion (October 24) wraps up the month with contemporary percussion works by Steve Reich, Oliver Tarpaga and Kendall Williams.

Mashpee Oktoberfest

When: October 3, 2026, 10 a.m. to 4 p.m. (rain date October 4 from 11 a.m. to 4 p.m.)

Where: Mashpee Commons Green, Mashpee MA

Admission: Free; food and beverages for sale

More Info: Mashpee Oktoberfest

The Town of Mashpee's annual Oktoberfest brings a full day of fall fun to the Village Green at Mashpee Commons.

Browse the work of local artisans and crafters, grab something tasty from the food trucks, listen to live music, join in the games, and stop by the biergarten for a little German-style celebrating.

SandwichFest

When: October 3, 2026, 10 a.m. to 3 p.m.

Where: Water Street, Sandwich, MA

Admission: Free

More Info: SandwichFest

SandwichFest features lots of fabulous food, a beer and wine tent, juried artisans and crafters, activities for the kids, and a live music PorchFest extravaganza. 

No doubt this will be a fun time for all again this year - as it always is!

Witches on the Water Costumed Paddle Event

When: October 3, 2026, 2 p.m. to 4 p.m.

Where:  Oyster Pond Beach, 80 Stage Harbor Rd, Chatham MA

Admission: Free for spectators; entry fee and fundraising requirement for paddlers

More Info: Witches on the Water

Witches on the Water ("WOW"), one of Cape Cod's premier non-profit organizations, definitely puts the fun in fundraiser!

Paddlers: Come dressed in your finest witchy regalia (or whatever character you choose to be), bring your own SUP (or kayak or paddle boat or any other self-powered aquatic vehicle). This isn't a race, it's just a fun paddle parade!

Spectators: Prefer to stay on dry land? Not a problem! Everyone is welcome to watch the fabulously-costumed paddlers parade around Oyster Pond. No admission fee is required for spectators. (Donations are always welcomed and gratefully accepted!)

In addition to a whole bunch of magical witches on SUPs, the event will also feature the ever-enchanting DJ Stephanie Viva, spellbinding live music, fantastical food trucks, mysterious raffles, and lots more! 

Tunes & Tales on the Trails

When: October 3, 2026, 1 p.m. to 4 p.m.

Where: Wellfleet Bay Wildlife Sanctuary, 291 State Highway Route 6, South Wellfleet MA

Admission: Free for Mass Audubon members; non-members $8 adults, $5 seniors, $3 children ages 2-12

More Info: Tunes & Tales on the Trails

Take a fall walk through Wellfleet Bay Wildlife Sanctuary, and don't be surprised if you come across a musician, poet or storyteller along the trail.

Different performers will be stationed around the sanctuary throughout the afternoon, with a new mix each hour. You can drop in for part of the event or spend the whole afternoon wandering the trails, listening to music and stories, and enjoying the sanctuary in autumn.

There'll also be a Nature Play Area for kids and an ice cream cart for anyone who thinks a trail walk deserves a treat at the end.

A Different Drummer Craft Fairs

When: October 3 & 4, 2026, 10 a.m. to 4 p.m.

Where: Drummer Boy Park, 773 Old Kings Highway (Rt. 6A), Brewster MA

Admission: Free

More Info: A Different Drummer Craft Fairs

A Different Drummer Craft Fairs feature more than 40 of Cape Cod and New England's best crafters and artists.

What will you find at these fairs? A wonderful selection of artwork, books, candles, clothing, fiber arts, glass, jewelry, metal work, mixed media, pet items, photography, soaps, pottery, toys, woodwork, and much more!

Vinegrass Music Festival

When: October 4, 2026, 11 a.m. to 6 p.m.

Where: Truro Vineyards, 11 Shore Road, N. Truro, MA

Admission:  $50-$60; children 14 and under are free when accompanied by an adult

More Info: Vinegrass Music Festival

This popular annual event at Truro Vineyards showcases the sounds of Americana, Bluegrass, & Folk (a/k/a "American Roots Music").  

This year's festival features performances by up-and-coming, talented artists - along with lots of yummy eats and Truro Vineyards' wines, Twenty Boat Rum, and Dry Line Gin available for purchase.

Love Local Fest

When: October 4, 2026, 11 a.m. to 4 p.m.

Where: Aselton Park on Hyannis Harbor

Admission: Free

More Info: LoveLiveLocal

The autumn Love Local Fest brings the Cape Cod community together for free, family-friendly fun while also supporting local businesses.

This popular event features local artists, brands, makers and the small businesses that sell them, along with food trucks, a craft beverage garden, live music, and kids activities — all overlooking the beautiful Hyannis Harbor.

Haunted Hallows + Halloweentown Market

When: Fridays & Saturdays, October 9 - 31, 2026, 5 p.m. to 9 p.m.

Where: Village Green at Mashpee Commons, 4 Job's Fishing Road, Mashpee MA

Admission: Halloweentown Market is free to browse; Haunted Hallows requires a ticket

More Info: Haunted Hallows

Friday and Saturday nights get a little spooky at Mashpee Commons in October.

Browse local vendors and makers at the Halloweentown Market, then head into Haunted Hallows if you're ready for something scarier. This immersive Halloween walkthrough lets you choose your scare level before you go in, so you decide how intense you want the experience to be.

And on Halloween day, Mashpee Commons wraps up the month with its annual Halloween Fun celebration, including live music, kids' activities, costume contests, a parade and trick-or-treating at the shops.

Taylor-Bray Farm's Fall Festival

When: October 10, 2026, 10 a.m. to 4 p.m. (rain date Oct. 11)

Where: Taylor Bray Farm, 108 Bray Farm Road North, Yarmouth Port MA

Admission: Free. Suggested parking donation $5

More Info: Taylor Bray Farm Fall Festival

Back again this year will be all the good, old-fashioned fun Taylor Bray Farm's Fall Festival is known for: hayrides, a pumpkin patch, games for the kids, tasty refreshments, and visits with all the friendly farm animals.

Donations are greatly appreciated and go toward upkeep of the farm, feeding and care of the animals, and the farm's educational programs. So please chip in $5 for parking - and a little more, if you're able!

*Note: No dogs are allowed at the farm on festival day.

Cobb House Museum & Windmill Village Open House

When: October 10, 2026, 1 p.m. to 4 p.m.

Where: Cobb House Museum, 739 Lower Road, and Windmill Village, 51 Drummer Boy Road, Brewster MA

Admission: Free

More Info: Cobb House & Windmill Village Open House

Here’s a chance to explore two of Brewster’s historic sites in one afternoon.

Tour the Cobb House Museum and Woodworking Shop, then head over to Windmill Village to see the old windmill, historic buildings and blacksmith shop. Along the way, you can browse exhibits and artifacts from Brewster’s past and meet the miller and blacksmith at Windmill Village.

Best of all, admission to both locations is free for the day.

Outermost Roots & Blues Festival

When: October 10, 2026; gates open at 11 a.m.

Where: Nauset Beach, Orleans MA

Tickets: General admission $70.00 plus fees; VIP and kids’ tickets also available

More Info: Outermost Roots & Blues Festival

Spend an October day at Nauset Beach listening to roots, blues, Americana and folk music performed by national touring acts and regional musicians.

Along with the music, there'll be local food vendors, beer and other beverages, plus a dedicated family area with games and activities for kids.

Centerville Village Fest

When: October 10, 2026, 10 a.m. to 1 p.m.

Where: Main Street, Centerville MA

More Info: Centerville Village Fest

Village Fest brings a whole bunch of fall fun to Main Street in Centerville.

The day includes free pumpkin decorating, face painting, sidewalk sales and a touch-a-truck with the COMM Fire Department and Smokey Bear.

You can also wander through Scarecrow Alley, take one of the spooky village tours, and catch the Blessing of the Animals.

Cape Cod Marathon Weekend

When: October 10 & 11, 2026

Where: Races start and finish at Mullen Hall School, 130 Katharine Lee Bates Road, Falmouth MA

More Info: Cape Cod Marathon Weekend

Cape Cod Marathon Weekend brings runners to Falmouth for two days of races, including the half marathon, full marathon, marathon relay, 5K and kids' race.

The marathon course winds through Falmouth and along the Nantucket Sound shoreline, passing Nobska Light and offering plenty of beautiful Cape scenery along the way.

Not running? Come out and cheer them on!

*Note: Check the event website (link above) for race times, course maps and spectator information before choosing where to watch.

Pumpkin Fest

When: October 10 & 11, 2026, 10 a.m. to 2 p.m.

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

Admission: Free

More Info: Pumpkin Fest at Sandwich Glass Museum

This is Sandwich Glass Museum's original and most popular outdoor festival fundraiser retail event of the year, featuring glass pumpkins and other autumn/Halloween-themed handblown glass artwork from local and regional studio glass artists.

The event will be held both Saturday and Sunday under the festival tent on the Museum lawn, rain or shine.

*Also happening at Sandwich Glass Museum this month: Design Your Own Glass Pumpkin sessions, Halloween-themed glass workshops, and other hands-on glassworking classes. See the museum's classes and workshops calendar for details.

Yarmouth Seaside Festival

When:  October 10 - 12, 2026

Where: Various venues around town

Admission: Free

More Info: Yarmouth Seaside Festival

Yarmouth Seaside Festival is a highlight of Columbus Day weekend on Cape Cod!

This annual extravaganza has tons of fun activities for the whole family, including old favorites like an arts and crafts fair, rides and games for the kids, food vendors, a sand-sculpting contest, canoe and kayak races, a beach bonfire, and a big fireworks display at Seagull Beach.

Pumpkin People in the Park

When: October 14 - November 1, 2026

Where: Kate Gould Park, Main Street, Chatham MA

Admission: Free

More Info: Pumpkin People in the Park

Every October, some unusual characters take up residence in Kate Gould Park!

Local businesses, nonprofits and community members create imaginative "Pumpkin People" displays that fill the park through Halloween.

Stop by any time during the display dates to see what this year's pumpkin people look like. They're always fun, and usually good for a laugh or two.

Women’s Week in Provincetown

When: October 12 - 18, 2026; some events begin October 9

Where: Various venues in Provincetown MA

Admission: Varies by event

More Info: Women’s Week Provincetown

Women’s Week brings hundreds of events to Provincetown for a celebration of women, community, arts and entertainment.

This year's lineup will include comedy, live music, theater, author events, art happenings, workshops, social gatherings and plenty more at venues all around town. With more than 300 individual events planned, there’s a whole lot happening over the course of the week.

Sins, Sips, and Secrets

When: October 15, 22 & 29, 2026, 6 p.m.

Where: Falmouth Museums on the Green, 55-65 Palmer Avenue, Falmouth MA

Admission: $35 members; $40 non-members. Advance registration required.

More Info: Sins, Sips, and Secrets

Spend an October evening exploring the darker side of Falmouth's past inside the 1790 Dr. Francis Wicks House.

As you move from room to room, you'll hear different tales drawn from old diaries, newspaper accounts and other historical records, including stories about strange happenings, wayward travelers and things that once went bump in the night.

Drinks and appetizers are included, and they'll be available beginning at 5:30 p.m. before the 6 p.m. tour. Space is limited to just 15 people per tour, so advance registration is a must.

Alfred Hitchcock's Psycho in Concert

When: October 17, 2026 at 7:30 p.m.; October 18 at 3 p.m.

Where: Barnstable Performing Arts Center, 744 West Main Street, Hyannis MA

Tickets: Prices vary by seating section

More Info: Alfred Hitchcock's Psycho in Concert

Talk about a different way to experience a classic horror movie!

Watch Alfred Hitchcock's Psycho on the big screen while Cape Symphony, conducted by Alyssa Wang, performs Bernard Herrmann's famously chilling score live and perfectly synchronized with the film.

And yes, those nerve-jangling strings that make the shower scene even more terrifying? They'll be coming from the orchestra right there in the theater. How cool is that?!

Wellfleet OysterFest

When:  October 17 & 18, 2026, 10 a.m. to 5 p.m. both days

Where: Main Street, Wellfleet, MA

Tickets: $35; children 12 and under are free but need their own free ticket, which must be reserved

More Info: Wellfleet OysterFest 

The ever-popular OysterFest is back for 2026, once again bringing shellfish lovers from near and far to celebrate the salty, succulent, world-renowned Wellfleet oyster.

What about the famous "Shuck Off"? It's back again this year - along with lots of local cuisine, a fine art and craft fair, educational non-profit booths, children’s activities, and live music.

Oktoberfest in Chatham

When: October 17, 2026

Where: Kate Gould Park and Town Hall Parking Lot, Chatham MA

Admission: Free; food and beverages for purchase

More Info: Oktoberfest in Chatham

Chatham's popular Oktoberfest is a free, family friendly day in downtown Chatham featuring live music, beer and wine, food trucks and tents, family activities and Pumpkin People in the Park.

*Tip: If you plan to enjoy an adult beverage or two, please don't drive!

Hyannis Open Streets

When: October 18, 2026, noon to 4 p.m. (rain date October 25)

Where: Main Street and Village Green, Hyannis

Admission: Free

More Info: Hyannis Open Streets

Remember when your parents warned you, "Don't play in the street!"? Well, this is one day when it's okay - encouraged, actually - for you to do just that.

Beginning at noon, Main Street in downtown Hyannis will be closed to auto traffic, allowing everyone to walk, run, bike, dance and play in the street!

There'll also be lots of family friendly activities on Main Street and at the Village Green, along with food, shopping, and live performances. Fun for all on an October day!

Spooky Knights at Heritage Museums & Gardens

When: October 23, 2026, 4:30 to 8:30 p.m.; October 24, 2026, 3:30 to 8:30 p.m.

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

Admission: $15 per person; children age 2 and under free. Timed-entry tickets required.

More Info: Spooky Knights Community Halloween Fundraiser

After dark, Heritage Museums & Gardens gets a Halloween makeover for two evenings of family-friendly fun.

Come in costume and dance to DJ Ooch, play carnival-style games, get your face painted or a temporary tattoo, make a take-home craft, and hop aboard the carousel, where even the horses get dressed up for Halloween. There'll also be fire pits, seasonal decorations and plenty of fun photo ops.

Best of all, ticket proceeds help support Sandwich Middle High School student groups and activities.

Apple Butter-Making Class at Green Briar

When: October 24, 2026, 10 a.m. to noon

Where: Green Briar Nature Center & Jam Kitchen, 6 Discovery Hill Road, East Sandwich MA

Admission: $85 members; $95 non-members

More Info: Apple Butter-Making Class

Roll up your sleeves and spend the morning making homemade apple butter in Green Briar’s historic 1903 Jam Kitchen.

During the family-friendly class, you'll make apple butter "from scratch", cooking on the Jam Kitchen's old cast-iron burners that date back more than a century. At the end of the class, you'll have 4 to 6 jars of your homemade apple butter to take with you. 

All materials are provided, and advance registration is required. The registration fee includes one adult and one child aged 6 or older.

Roots: A Farm to Circus Show

When: October 24 & 25, 2026, 1 p.m.

Where: Tony Andrews Farm, 394 Old Meeting House Road, East Falmouth MA

Tickets: Adults $20; children $15; age 2 and under free

More Info: Roots: A Farm to Circus Show

What happens when you mix a working Cape Cod farm with acrobats, aerialists and clowns? You get Roots: A Farm to Circus Show.

Payomet’s Cirque by the Sea takes the audience along on the story of a young farmer who inherits the family farm, dreams up some big plans, then discovers there may be more to farming than turning a quick profit.

The 60-minute outdoor show combines circus performances with a story about regenerative farming. Come early or linger afterward to wander around Tony Andrews Farm.

Cape Cod Book Festival

When: October 24, 2026, 10 a.m. to 4 p.m.; October 25, 2026, beginning at 1:30 p.m.

Where: Cotuit Center for the Arts, 4404 Falmouth Road, Cotuit MA (Saturday); Cape Cod Community College, 2240 Iyannough Road, West Barnstable MA (Sunday)

Admission: Saturday: $35 full-day pass or $20 per session; Sunday tickets sold separately. Cape Cod Community College students attend Sunday free.

More Info: Cape Cod Book Festival

Book lovers have two days of author conversations to choose from at this year's Cape Cod Book Festival.

Saturday's lineup includes Kwame Alexander, Isaac Fitzgerald, Victoria Christopher Murray, John Searles and Nathaniel Philbrick, with discussions ranging from Johnny Appleseed and the California Gold Rush to Marilyn Monroe and Helen Gurley Brown.

On Sunday, mystery writers Hank Phillippi Ryan and Joseph Finder talk crime and thriller writing, followed by historical-fiction authors Ariel Lawhon and Kristin Harmel.

Book signings and photo ops follow the talks. If you'd like a book autographed, note that only books purchased at the festival will be signed.

Halloween on the Windmill Green

When: October 24, 2026; time TBA

Where: Windmill Green, Eastham MA

Admission: Free

More Info: Town of Eastham Recreation

Halloween takes over Eastham's Windmill Green the Saturday before the big day, with local businesses, Town departments and community groups setting up trick-or-treat stations around the Green.

Kids come in costume and make their way from table to table, filling their buckets with candy as they go.  And the fun goes well beyond candy collecting, with music and dancing, Halloween games, a costume contest and a pumpkin-carving contest all part of the event.

It's a popular Eastham tradition for locals and visiting families, too.

Cemetery Lantern Tour 

When: October 25, 2026, at 4:30, 5 & 5:30 p.m.

Where: First Congregational Church Cemetery, Harwich Center MA; park and meet at Brooks Academy Museum, 80 Parallel Street, Harwich MA

Admission: $10; advance ticket purchase recommended

More Info: Cemetery Lantern Tour

Step back into Revolutionary War-era Harwich on this lantern tour through the First Congregational Church Cemetery.

Along the way, you'll meet costumed interpreters portraying Revolutionary War soldiers and their wives, who'll tell you about their lives and experiences during the war.

Each tour lasts about 30 minutes, and space is limited. You can pay at the tour if space is still available, but buying your ticket ahead of time is the best way to be sure you get in.

An Evening with Washington Irving: An Interactive Performance

When: October 27, 2026, 7 p.m. to 8:30 p.m.

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

Tickets: $10 plus small online fee

More Info: An Evening with Washington Irving

Meet Washington Irving, the man who created Ichabod Crane, the Headless Horseman and Rip Van Winkle, in this interactive one-man performance.

Actor and scholar John Dennis Anderson portrays Irving as he tells stories about Irving's writing, travels and adventures, including how some of his best-known tales came to be.

After the performance, Anderson will take questions first in character as Irving, then as the scholar and performer behind the role.

Halloween Murder Mystery Dinner Train

When: October 29, 2026, 5:30 p.m.; October 31, 2026, 4:30 p.m.

Where: Cape Cod Central Railroad, 252 Main Street, Hyannis MA

Tickets: From $114.99

More Info: Halloween Murder Mystery Dinner Train

There’s been a murder aboard the train, and it’s up to you and your fellow passengers to figure out whodunit!

As the train rolls along, actors mingle with passengers, clues emerge and suspects reveal themselves between courses of a four-course dinner.

This Halloween mystery, Evil Never Dies, gives everyone a chance to question suspects, piece together the evidence and decide who should be arrested.

*Note: The whole experience lasts about 3 to 3½ hours and is recommended for ages 13 and up.

Dennis Halloweenpalooza

When: October 31, 2026, noon to 4 p.m.

Where: Johnny Kelley Park, 180 Old Bass River Road, South Dennis MA

Admission: Free

More Info: Dennis Halloweenpalooza

Put on your Halloween costume and head to Johnny Kelley Park for an afternoon of Halloween fun for kids and grown-ups alike.

Halloweenpalooza features a candy haunt for the kids, a cornhole tournament, food trucks, live music and a beer garden. Costumes are encouraged, so don't be shy about getting into the Halloween spirit!

*See: My Activities & Attractions guide for lots more fun on Cape Cod in October!

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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!