Cape Cod Fall Events

Michael Leighton
Michael Leighton
Published on September 6, 2019

The summer season is not quite over, but Cape Cod fall events are right around the corner! There are plenty of activities for you and the family to enjoy on beautiful Cape Cod while the weather is still mild and the days are a little longer. Check out our list of Cape Cod fall events to keep you busy this season!

September Cape Cod Fall Events

Eastham Windmill Weekend

Date: Friday, September 6 – Sunday September 8th

Time: Throughout the day, all weekend long

Location: Windmill Green and Bandstand Eastham: Route 6, Eastham

Eastham Windmill Weekend Link

7th Annual Cape Cod Comedy Festival

Date: Saturday, September 7

Time: 5:00 pm – 10:00 pm

Location: Cape Cod Fairgrounds: 1220 Nathan Ellis Highway, East Falmouth

Cape Cod Comedy Festival Link

All Around the Common in Yarmouth Port

Date: Sunday, September 8

Time: 1:00 pm – 4:00 pm

Location: The Common on Strawberry Lane, Yarmouth

All Around the Common Link

Cape Cod Roots & Blues Festival

Date: Saturday, September 14

Time: 12:00 pm – 6:00 pm

Location: Nauset Beach: 250 Beach Road, Orleans

Cape Cod Roots & Blues Festival Link

Provincetown Book Festival

Date: Saturday, September 14 – Sunday September 15

Time: 10:30 am – 5:30 pm

Location: Provincetown Public Library: 356 Commercial Street, Provincetown

Provincetown Book Festival Link

Harwich Cranberry Arts & Music Festival

Date: Saturday, September 14 & Sunday, September 15

Time: Throughout the day Saturday & Sunday

Location: The Harwich Community Center Field: 100 Oak Street, Harwich

Harwich Cranberry Arts & Music Festival Link

Fall Fest Friday Event at Heritage Museums & Gardens

Date: Friday, September 20

Time: 2:00 pm – 7:00 pm

Location: Heritage Museums & Gardens: 67 Grove Street, Sandwich

Fall Fest Friday Event Link

Love Yoga Fest

Date: Friday, September 20

Time: 5:30 pm

Location: Sea Crest Beach Hotel: 350 Quaker Road, North Falmouth

Love Yoga Fest Link

Oktoberfest 2019 / FUNK-toberfest

Date: Saturday, September 21

Time: 11:00 am – 4:00 pm

Location: Cape Cod Beer: 1336 Phinneys Lane, Hyannis

Oktoberfest / FUNK-toberfest Link

Block Party at the Dog

Date: Saturday, September 21

Time: 12:00 pm – 5:00 pm

Location: Sea Dog Brew Pub: 23 Whites Path, South Yarmouth

Block Party at the Dog Link

8th Annual Cape Cod Brew Fest

Date: Saturday, September 21

Time: 10:00 am – 1:30 pm

Location: Cape Cod Fairgrounds, 1220 Nathan Ellis Highway, East Falmouth

8th Annual Cape Cod Brew Fest Link

Grape Stomp and Music Fest at Truro Vineyards with the Dirty Water Dance Band

Date: Sunday, September 22

Time: Band plays 2:00 pm – 6:00 pm; Grape Stomp at 3:00 pm

Location: Truro Vinyards & South Hollow Spirits: 11 Shore Road (Route 6), North Truro

Grape Stomp and Music Fest Link

6th Annual Vinegrass Music Festival

Date: Sunday, September 29

Time: 12:00 pm – 6:00 pm

Location: Truro Vineyards & South Hollow Spirits: 11 Shore Road (Route 6), North Truro

Vinegrass Music Festival Link

Love Local Fest

Date: Sunday, September 29

Time: 11:00 am – 6:00 pm

Location: Michael K. Aselton Memorial Park, Hyannis

Love Local Fest Link

October  Cape Cod Fall Events

Fall Family Festival hosted by Ponderosa Marketplace

Date: Saturday, October 5

Time: 10:00 am – 2:00 pm

Location: The Marketplace Home and Garden Center: 4850 State Highway Route 6, Eastham

Fall Family Festival Link

Farm Fest at Chatham Bars Inn Farm

Date: Saturday, October 5

Time: 4:00 pm – 7:00 pm

Location: Chatham Bars Inn Farm: 3034 Main Street, Brewster

Farm Fest at Chatham Bars Inn Farm Link

Fall Festival at Taylor Bray Farm

Date: Saturday, October 12

Time: 10:00 am – 3:00 pm

Location: Taylor – Bray Farm: 108 Taylor Bray Farm Road, Yarmouth Port

Fall Festival at Taylor Bray Farm Link

Brewster Potato Fest

Date: Saturday, October 12

Time: 10:00 am – 2:00 pm

Location: First Parish Brewster Unitarian Universalist Church: 1960 Main Street, Brewster

Brewster Potato Fest Link

Columbus Day Weekend Fine Arts and Crafts Show

Date: Saturday, October 12

Time: 10:00 am – 4:00 pm

Location: Drummer Boy Park: Route 6A, Brewster

Columbus Day Weekend Fine Arts & Crafts Show Link

Harwich – Dennis Rotary Scallop Festival

Date: Saturday, October 12

Time: 11:00 am – 7:00 pm

Location: The Weatherdeck Restaurant

Harwich – Dennis Rotary Scallop Festival Link

Yarmouth Seaside Festival

Date: Saturday, October 12 – Monday October 14

Time: Throughout the day every day

Location: Joshua Sears Memorial Field, South Yarmouth

Yarmouth Seaside Festival Link

Women’s Week Provincetown

Date: Monday, October 14 – Sunday, October 20

Time: All day, throughout the week

Location: Throughout Provincetown

Women’s Week Link

Oktoberfest – Chatham

Date: Saturday , October 19

Time: 11:30 am – 5:30 pm

Location: Kate Gould Park, 15 Chatham Bars Ave, Chatham

Oktoberfest – Chatham Link

2019 Wellfleet OysterFest

Date: Saturday Oct 19 – Sun Oct 20

Time: Throughout the day Saturday and Sunday

Location: All along Main Street, Wellfleet

Wellfleet OysterFest Link

Pumpkin People in the Park

Date: October 20 – October 28

Time: All Day

Location: Kate Gould Park, Chatham

Pumpkin People in the Park Link

Giant Jenga Tournament

Date: Thursday, October 24

Time: 6:00 pm – 9:00 pm

Location: Hog Island Beer Company: 28 West Road, Orleans

Giant Jenga Tournament Link

2019 Orleans Surf Film Festival

Date: Friday, October 25

Time: 5:30 pm – 10:30 pm

Location: Hog Island Beer Company: 28 West Road, Orleans

Orleans Surf Film Festival Link

November  Cape Cod Fall Events

Trolley Tour Taste of Yarmouth

Date: Saturday, November 9

Time: 12:00 pm – 7:00 pm

Location: All around the town of Yarmouth

Trolley Tour Taste of Yarmouth Link

Eastham Turnip Festival

Date: Saturday, November 23

Time: Not listed yet – Check website for times closer to event date

Location: Nauset Regional High School: 100 Cable Road, Eastham

Eastham Turnip Festival Link

Cape Cod Fall Events

Even though the summer season is coming to a close, you can still enjoy the beautiful bayside beaches throughout the fall that Cape Cod is known for. Check out our blog, “Cape Cod Coffee Shops Open in the Off Season” to find out where to get a cup of coffee year round now that the high season has ended.

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