Events and Things to do in Orleans, MA

Search for something you love or check out popular events in your area.

Lenny Clarke & Steve Sweeney Stand-up Comedy Show ONE NIGHT ONLY Sept 19th
Saturday at 8:00 PM
Thumpertown Beach · Four Points by Sheraton Eastham Cape Cod
Lenny Clarke & Steve Sweeney Stand-up Comedy Show ONE NIGHT ONLY Sept 19th
Saturday at 8:00 PM
Thumpertown Beach · Four Points by Sheraton Eastham Cape Cod
Chatham Bars Inn Farm Fall Frolic
Sun, Oct 11, 11:00 AM
East Brewster · Chatham Bars Inn Farm
Chatham Bars Inn Farm Fall Frolic
Sun, Oct 11, 11:00 AM
East Brewster · Chatham Bars Inn Farm
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
Friends of James Beard Foundation Dinner at the Chatham Bars Inn Farm
Saturday at 5:00 PM
East Brewster · Chatham Bars Inn Farm
Friends of James Beard Foundation Dinner at the Chatham Bars Inn Farm
Saturday at 5:00 PM
East Brewster · Chatham Bars Inn Farm
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
12th Vinegrass Music Festival
Sun, Oct 4, 11:00 AM
Massachusetts · Truro Vineyards
12th Vinegrass Music Festival
Sun, Oct 4, 11:00 AM
Massachusetts · Truro Vineyards
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
Mahjong Brunch
Sun, Oct 11, 10:00 AM
Quitnesset · Chatham Bars Inn
Mahjong Brunch
Sun, Oct 11, 10:00 AM
Quitnesset · Chatham Bars Inn
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
Strong Island Birding Walk with James Junda
Saturday at 2:00 PM
Massachusetts · Strong Island
Strong Island Birding Walk with James Junda
Saturday at 2:00 PM
Massachusetts · Strong Island
Isabelle O'Connell in Concert
Saturday at 7:00 PM
Massachusetts · Wellfleet Preservation Hall
Isabelle O'Connell in Concert
Saturday at 7:00 PM
Massachusetts · Wellfleet Preservation Hall
A Taste of Charm: Taco Night
Wed, Sep 30, 5:00 PM
East Brewster · The Charm on Main
A Taste of Charm: Taco Night
Wed, Sep 30, 5:00 PM
East Brewster · The Charm on Main
A Taste of Charm: Plant-Powered Kitchen
Wed, Oct 14, 5:00 PM
East Brewster · The Charm on Main
A Taste of Charm: Plant-Powered Kitchen
Wed, Oct 14, 5:00 PM
East Brewster · The Charm on Main
Manhattan Short Film Festival SATURDAY, 10/3
Sat, Oct 3, 2:30 PM
Massachusetts · Wellfleet Preservation Hall
Manhattan Short Film Festival SATURDAY, 10/3
Sat, Oct 3, 2:30 PM
Massachusetts · Wellfleet Preservation Hall
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
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
A Night of Comedy with Paul Nardizzi
Sat, Oct 10, 7:30 PM
Quitnesset · Chatham Bars Inn
A Night of Comedy with Paul Nardizzi
Sat, Oct 10, 7:30 PM
Quitnesset · Chatham Bars Inn
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
Pioneers of Longevity
Thu, Sep 24, 5:00 PM
Rock Harbor · Gibson Sotheby's International Realty
Pioneers of Longevity
Thu, Sep 24, 5:00 PM
Rock Harbor · Gibson Sotheby's International Realty

Trends in Orleans

Explore more trends

Frequently asked questions about Orleans

What are the best events to attend?

According to Eventbrite, the best events are:

Lenny Clarke & Steve Sweeney Stand-up Comedy Show ONE NIGHT ONLY Sept 19th

Chatham Bars Inn Farm Fall Frolic

9th ANNUAL CHRIS DIOZZI OPEN | 2026

COMEDIAN JUSTON MCKINNEY

Which events are currently trending in Orleans?

The trending searches this month in Orleans are:

Which events are coming up?

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

Love Farms Harvest Festival: Honey Week

Strong Island Birding Walk with James Junda

Friends of James Beard Foundation Dinner at the Chatham Bars Inn Farm

Isabelle O'Connell in Concert

Lenny Clarke & Steve Sweeney Stand-up Comedy Show ONE NIGHT ONLY Sept 19th

Lenny Clarke & Steve Sweeney Stand-up Comedy Show ONE NIGHT ONLY Sept 19th

Chatham Bars Inn Farm Fall Frolic

Chatham Bars Inn Farm Fall Frolic

9th ANNUAL CHRIS DIOZZI OPEN | 2026

9th ANNUAL CHRIS DIOZZI OPEN | 2026

Friends of James Beard Foundation Dinner at the Chatham Bars Inn Farm

Friends of James Beard Foundation Dinner at the Chatham Bars Inn Farm

COMEDIAN JUSTON MCKINNEY

COMEDIAN JUSTON MCKINNEY

12th Vinegrass Music Festival

12th Vinegrass Music Festival

Love Farms Harvest Festival: Oyster Week

Love Farms Harvest Festival: Oyster Week

Mahjong Brunch

Mahjong Brunch

Love Farms Harvest Festival: Apple Week

Love Farms Harvest Festival: Apple Week

Strong Island Birding Walk with James Junda

Strong Island Birding Walk with James Junda

Isabelle O'Connell in Concert

Isabelle O'Connell in Concert

A Taste of Charm: Taco Night

A Taste of Charm: Taco Night

A Taste of Charm: Plant-Powered Kitchen

A Taste of Charm: Plant-Powered Kitchen

Manhattan Short Film Festival SATURDAY, 10/3

Manhattan Short Film Festival SATURDAY, 10/3

Love Farms Harvest Festival: Oktoberfest

Love Farms Harvest Festival: Oktoberfest

Love Farms Harvest Festival: Pickle Week

Love Farms Harvest Festival: Pickle Week

A Night of Comedy with Paul Nardizzi

A Night of Comedy with Paul Nardizzi

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

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

Love Farms Harvest Festival: Honey Week

Love Farms Harvest Festival: Honey Week

Pioneers of Longevity

Pioneers of Longevity

Things to do around Orleans

Trends in Orleans

1. Mothers day

2. Hog island brewery

3. Town cove tap house

4. Out of office

5. Craft fairs

6. Concerts

7. Class

8. Yoga

9. Workshops

10. Wellington square

11. Weekend

12. Walk for truth

What are the best events to attend?

Which events are currently trending in Orleans?

Which events are coming up?