What are the Festivals happening in Oakland This Weekend February 13-15 2026?

Here are the Festivals happening this weekend February 13-15 2026 in Oakland:: - Oakland's Winter Fest & Wine Walk is happening on Sat 14 Feb 2026 from 11:00 AM onwards at Oakland, MD, United States, Maryland 21550 - Cupid's Corner: A Handmade Market! is happening on Sat 14 Feb 2026 from 10:00 AM onwards at 108 S 2nd Street, Oakland, MD, United States, Maryland 21550 - St. Peter's Second Annual Chili Cook-off is happening on Sat 14 Feb 2026 from 11:00 AM onwards at 208 S. 4th Street , Oakland, MD, United States, Maryland 21550

What are the top Festivals happening in Oakland?

Here are the top Festivals in Oakland:: - Oakland's Winter Fest & Wine Walk is happening on Sat 14 Feb 2026 from 11:00 AM onwards at Oakland, MD, United States, Maryland 21550 - 2026 MS/NRP Deep Creek Dunk is happening on Sat 21 Feb 2026 from 11:00 AM onwards at 19746 Garrett Hwy, Oakland, MD, United States, Maryland - 2026 Snallygaster -- The 5th Annual! is happening on Sat 12 Sep 2026 from 7:00 AM onwards at 103 Town Park Ln, Oakland, MD 21550-1837, United States - Cupid's Corner: A Handmade Market! is happening on Sat 14 Feb 2026 from 10:00 AM onwards at 108 S 2nd Street, Oakland, MD, United States, Maryland 21550 - St. Peter's Second Annual Chili Cook-off is happening on Sat 14 Feb 2026 from 11:00 AM onwards at 208 S. 4th Street , Oakland, MD, United States, Maryland 21550

What are the Festivals happening in Oakland this February 2026?

Here are the Festivals happening in Oakland in February 2026 :: - Oakland's Winter Fest & Wine Walk is happening on Sat 14 Feb 2026 from 11:00 AM onwards at Oakland, MD, United States, Maryland 21550 - 2026 MS/NRP Deep Creek Dunk is happening on Sat 21 Feb 2026 from 11:00 AM onwards at 19746 Garrett Hwy, Oakland, MD, United States, Maryland - Cupid's Corner: A Handmade Market! is happening on Sat 14 Feb 2026 from 10:00 AM onwards at 108 S 2nd Street, Oakland, MD, United States, Maryland 21550 - St. Peter's Second Annual Chili Cook-off is happening on Sat 14 Feb 2026 from 11:00 AM onwards at 208 S. 4th Street , Oakland, MD, United States, Maryland 21550

Oakland, MD Festival Guide 2026 | Find Culture & Street Fairs In Oakland, MD

AllEvents · 2026-02-10T22:22:02+00:00

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Festivals in Oakland

Sat, 14 Feb, 2026 - 11:00 AM

Oakland's Winter Fest & Wine Walk

Oakland, MD, United States, Maryland 21550

269+ Interested
Sat, 21 Feb, 2026 - 11:00 AM

2026 MS/NRP Deep Creek Dunk

19746 Garrett Hwy, Oakland, MD, United States, Maryland

138+ Interested
Sat, 12 Sep, 2026 - 07:00 AM

2026 Snallygaster -- The 5th Annual!

103 Town Park Ln, Oakland, MD 21550-1837, United States

17+ Interested
Sat, 14 Feb, 2026 - 10:00 AM

Cupid's Corner: A Handmade Market!

108 S 2nd Street, Oakland, MD, United States, Maryland 21550

24+ Interested
Sat, 14 Feb, 2026 - 11:00 AM

St. Peter's Second Annual Chili Cook-off

208 S. 4th Street , Oakland, MD, United States, Maryland 21550

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Festivals in Oakland

Festivals in Oakland

Festivals in Oakland

Oakland's Winter Fest & Wine Walk

2026 MS/NRP Deep Creek Dunk

2026 Snallygaster -- The 5th Annual!

Cupid's Corner: A Handmade Market!

St. Peter's Second Annual Chili Cook-off

Explore events by date

Festivals from nearby cities

West Virginia Mountaineers vs. UT Martin Skyhawks

DelFest - 4 Day Pass - with The Del McCoury Band, The Travelin' McCourys, Alison Krauss and more

Antique, Classic & Street Road Car Show

Grande Feature Parade

The Bacon Brothers

Oakland's Winter Fest & Wine Walk

Mountain Craft Days 2026

3rd Annual Summer Harvest Festival - Downtown Romney, WV

Greene County Fair Chaos in Coal Country Demolition Derby

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Here are the Festivals happening this weekend February 13-15 2026 in Oakland:

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Festivals from nearby cities

Festivals in Oakland

Festivals in Oakland

Festivals in Oakland

Oakland's Winter Fest & Wine Walk

2026 MS/NRP Deep Creek Dunk

2026 Snallygaster -- The 5th Annual!

Cupid's Corner: A Handmade Market!

St. Peter's Second Annual Chili Cook-off

Explore events by date

Festivals from nearby cities

West Virginia Mountaineers vs. UT Martin Skyhawks

DelFest - 4 Day Pass - with The Del McCoury Band, The Travelin' McCourys, Alison Krauss and more

Antique, Classic & Street Road Car Show

Grande Feature Parade

The Bacon Brothers

Oakland's Winter Fest & Wine Walk

Mountain Craft Days 2026

3rd Annual Summer Harvest Festival - Downtown Romney, WV

Greene County Fair Chaos in Coal Country Demolition Derby

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Here are the Festivals happening this weekend February 13-15 2026 in Oakland:

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Festivals from nearby cities