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Events and Things to do in Osterville, MA

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Cape Cod Beer's Oyster Fest: Shuck! A Day of Oysters and Beer!
Sat, Oct 3, 12:00 PM
Barnstable Town · Cape Cod Beer
Cape Cod Beer's Oyster Fest: Shuck! A Day of Oysters and Beer!
Sat, Oct 3, 12:00 PM
Barnstable Town · Cape Cod Beer
Love Farms Harvest Festival: Honey Week
Saturday at 10:00 AM
Harbour Haven · Love Farms
Love Farms Harvest Festival: Honey Week
Saturday at 10:00 AM
Harbour Haven · Love Farms
Love Farms Harvest Festival: Apple Week
Sat, Sep 26, 10:00 AM
Harbour Haven · Love Farms
Love Farms Harvest Festival: Apple Week
Sat, Sep 26, 10:00 AM
Harbour Haven · Love Farms
Women & Water
Thu, Sep 24, 6:00 PM
Colonial Acres · 81 Willow Ave
Women & Water
Thu, Sep 24, 6:00 PM
Colonial Acres · 81 Willow Ave
9th ANNUAL CHRIS DIOZZI OPEN | 2026
Sat, Oct 17, 7:00 AM
New Boston · Dennis Highlands Golf Course
9th ANNUAL CHRIS DIOZZI OPEN | 2026
Sat, Oct 17, 7:00 AM
New Boston · Dennis Highlands Golf Course
Love Farms Harvest Festival: Oktoberfest
Sat, Oct 24, 10:00 AM
Harbour Haven · Love Farms
Love Farms Harvest Festival: Oktoberfest
Sat, Oct 24, 10:00 AM
Harbour Haven · Love Farms
Cape Cod Doxie Day After Party at Cape Cod Beer!
Sat, Sep 26, 3:00 PM
Barnstable Town · Cape Cod Beer
Cape Cod Doxie Day After Party at Cape Cod Beer!
Sat, Sep 26, 3:00 PM
Barnstable Town · Cape Cod Beer
Love Farms Harvest Festival: Oyster Week
Sat, Oct 10, 10:00 AM
Harbour Haven · Love Farms
Love Farms Harvest Festival: Oyster Week
Sat, Oct 10, 10:00 AM
Harbour Haven · Love Farms
JR Richards (DISHWALLA original singer)
Fri, Nov 6, 7:30 PM
Pine Tree Corner · The Listening Room of Cape Cod
JR Richards (DISHWALLA original singer)
Fri, Nov 6, 7:30 PM
Pine Tree Corner · The Listening Room of Cape Cod
Valley Grille Comedy Night
Saturday at 7:00 PM
Pine Tree Corner · Valley Grille
Valley Grille Comedy Night
Saturday at 7:00 PM
Pine Tree Corner · Valley Grille
An Evening With Music City’s Rising Stars
Saturday at 7:00 PM
Vineyard Highlands · Strand Theatre
An Evening With Music City’s Rising Stars
Saturday at 7:00 PM
Vineyard Highlands · Strand Theatre
Tony V at the Seacrest
Sat, Oct 17, 8:00 PM
Old Silver Beach · Sea Crest Beach Hotel
Tony V at the Seacrest
Sat, Oct 17, 8:00 PM
Old Silver Beach · Sea Crest Beach Hotel
Behind the Curtain With the Nashville Hit Makers
Tomorrow at 7:00 PM
Vineyard Highlands · Strand Theatre
Behind the Curtain With the Nashville Hit Makers
Tomorrow at 7:00 PM
Vineyard Highlands · Strand Theatre
CWB Coffee Connect
Tuesday at 8:00 AM
Old Silver Beach · Daily Brew Coffee House & Lounge
CWB Coffee Connect
Tuesday at 8:00 AM
Old Silver Beach · Daily Brew Coffee House & Lounge
Comedy Show at Marshland Too Restaurants
Sat, Oct 3, 7:30 PM
Massachusetts · 315 Cotuit Rd
Comedy Show at Marshland Too Restaurants
Sat, Oct 3, 7:30 PM
Massachusetts · 315 Cotuit Rd
Pieces of Me at Falmouth Academy
Sun, Sep 27, 6:00 PM
Sippewisset · Falmouth Academy
Pieces of Me at Falmouth Academy
Sun, Sep 27, 6:00 PM
Sippewisset · Falmouth Academy
Love Farms Harvest Festival: Pickle Week
Sat, Oct 3, 10:00 AM
Harbour Haven · Love Farms
Love Farms Harvest Festival: Pickle Week
Sat, Oct 3, 10:00 AM
Harbour Haven · Love Farms
Hand Knit Blanket Worskshop at Cape Cod Winery
Sun, Sep 27, 3:00 PM
Kingdom Hall · Cape Cod Winery
Hand Knit Blanket Worskshop at Cape Cod Winery
Sun, Sep 27, 3:00 PM
Kingdom Hall · Cape Cod Winery
COMEDIAN JUSTON MCKINNEY
Sat, Oct 3, 7:30 PM
Harwich Center · The 204 Cultural Arts Municipal Building
COMEDIAN JUSTON MCKINNEY
Sat, Oct 3, 7:30 PM
Harwich Center · The 204 Cultural Arts Municipal Building
26th Annual Heritage Award Celebration at Museums on the Green
Thu, Oct 1, 4:00 PM
Falmouth Heights · Falmouth Historical Society
26th Annual Heritage Award Celebration at Museums on the Green
Thu, Oct 1, 4:00 PM
Falmouth Heights · Falmouth Historical Society

1 of 385

Things to do around Osterville

Things to do in New Bedford

Things to do in Newport

Things to do in Fall River

Things to do in Plymouth

Things to do in Brockton

Things to do in Barnstable Town

Things to do in South Duxbury

Things to do in Taunton

Things to do in Somerset

Things to do in Newport East

Things to do in Provincetown

Things to do in Weymouth Town

Trends in Osterville

Explore more trends

1. Ostervilke stroll

Explore more trends

Frequently asked questions about Osterville

What are the best events to attend?

According to Eventbrite, the best events are:

Cape Cod Beer's Oyster Fest: Shuck! A Day of Oysters and Beer!

Love Farms Harvest Festival: Apple Week

9th ANNUAL CHRIS DIOZZI OPEN | 2026

Which events are currently trending in Osterville?

The trending searches this month in Osterville are:

ostervilke stroll

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Behind the Curtain With the Nashville Hit Makers

Love Farms Harvest Festival: Honey Week

Valley Grille Comedy Night

An Evening With Music City’s Rising Stars

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