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Orleans Events

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View events in Orleans on or after 8/5/2025

Annual Summner Fair

Where: The Federated Church of Orleans, 162 Main street, Orleans

When:

How Much: Free

Categories: Family/Children

Wednesday, August 6 – ANNUAL SUMMER FAIR featuring books, jewelry, yard sale items, toys, handcrafts, baked goods and super raffles featuring bundled gift certificates. Rain or shine!

First Friday's in Orleans

Where: Main Street, Orleans

When:
Friday, August 15, 2025,
Friday, August 22, 2025,

How Much: Free

Categories: Outdoor

First Fridays return June through September, featuring arts, music, and local vendors—and stores will be open until 8 PM for evening shopping.

Nauset Summer Craft Festival

Where: Nauset Regional Middle School, 70 Route 28, Orleans

When:
Sunday, August 10, 2025, 10:00 AM - 4:00 PM

How Much: Free

Categories: Festival

Experience Artistry at the Nauset Summer Craft Festival!Mark your calendars for a vibrant weekend of creativity as the Nauset Summer Craft Festival returns on August 9 & 10, 2025, at the spacious Nauset Regional Middle School along Route 28 in Orleans, MA. This annual f...read more

Eastwind Art Gallery Reopening!

Where: Eastwind Gallery, 34 Main Street, Orleans

When: Daily, -

How Much: Free

Categories: Arts

Eastwind Gallery Celebrates Its Spring Reopening April 24thAs spring arrives, so does Eastwind Gallery on Main Street in Orleans. Opening day is Thursday, April 24th, featuring an artists' exhibition of "New Beginnings." Stop in Thursday through Saturday between 11 am a...read more

Cape Cod Baseball League

Where: Cape Wide, Bourne, Brewster, Chatham, Cotuit, Falmouth, Harwich, Hyannis, Orleans, Wareham, Yarmouth

When: Daily, -

How Much: Free

Categories: Sports

This is the premier amateur baseball league in the nation since 1885. See the MLB stars of tomorrow throughout the summer Cape-wide, and admission is free. Two divisions of teams play across the Cape, beginning prior to the bridge in Wareham and stretch...read more

A Seaside Christmas in Orleans

Where: Orleans

When: Daily, -

How Much: Free

Categories: Holiday

The Orleans Chamber of Commerce kicks off its annual Seaside Christmas festivities with an array of holiday happenings on Friday November 29th, including Breakfast with Mrs. Claus, the arrival of Santa, Winterfest Orleans events and amazing holiday deals during Small ...read more

Outermost Friday Market in the Park

Where: The Village Green, Orleans

When:

How Much: Free

Categories: Festival

The Orleans Chamber of Commerce will host Outermost Friday in the Park on the village green at the corner of Main Street and Route 28. The free event will feature live music, DJs, food trucks, beer and wine and more than 30 local merchants and nonprofit groups.

Orleans Tree Lighting and Caroling

Where: Snows Library/Depot Square, Main St. , Orleans

When:

How Much: Free

Categories: Holiday

The Orleans Improvement Association, in partnership with the Orleans Chamber of Commerce, invites you to kick off the holiday season with us at our Annual Tree Lighting.

Santa Stampede

Where: Barley Neck, Orleans

When:

How Much: Adults $30, Children $15, Check website for registration

Categories: Outdoor

Santa Stampede dashes into town on Saturday, December 6, bringing holiday cheer and a fun run for all ages.

Art Cottages at the Orleans Market Square

Where: Art Cottages at the Orleans Market Square, 15 Old Colony Way, Orleans

When:

How Much: Free

Categories: Arts

Recognizing that the arts improve the quality of life for residents, contribute to the economic vitality of communities, and have the power to build healthier, more livable, more vital communities, Orleans resident Todd Thayer has established The Artist Cottages at Orle...read more


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