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Events and Things to do in Preston, MD

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Mother’s Day Tea 2026 | Pouring Into Generations
Sat, May 2, 12:00 PM
Easton · 10659 Hiners Ln
Mother’s Day Tea 2026 | Pouring Into Generations
Sat, May 2, 12:00 PM
Easton · 10659 Hiners Ln
Visit the Quaint Town of St. Michaels & Enjoy a Winery Tasting Tour
Thu, May 7, 9:00 AM
St. Michaels · St. Michaels Maryland
Visit the Quaint Town of St. Michaels & Enjoy a Winery Tasting Tour
Thu, May 7, 9:00 AM
St. Michaels · St. Michaels Maryland
Almost full
Turtle Paddle - 2026 - Sultana Education Foundation
Sat, Jun 13, 10:00 AM
Queen Anne · Tuckahoe State Park Boat Ramp
Almost full
Turtle Paddle - 2026 - Sultana Education Foundation
Sat, Jun 13, 10:00 AM
Queen Anne · Tuckahoe State Park Boat Ramp
Sales end soon
Realign: All-Inclusive 3-Day Women’s Retreat to Refresh & Recalibrate
Tomorrow at 3:30 PM
Royal Oak · Royal Oak
Sales end soon
Realign: All-Inclusive 3-Day Women’s Retreat to Refresh & Recalibrate
Tomorrow at 3:30 PM
Royal Oak · Royal Oak
Cookies With the Easter Bunny
Sat, Mar 28, 9:00 AM + 1 more
Bridgeville · T.S. Smith Orchard Point Market
Cookies With the Easter Bunny
Sat, Mar 28, 9:00 AM + 1 more
Bridgeville · T.S. Smith Orchard Point Market
Almost full
Headwaters of the Choptank Paddle - 2026 - Sultana Education Foundation
Sat, May 16, 10:00 AM
Greensboro · Greensboro Boat Ramp in the Greensboro Community Park
Almost full
Headwaters of the Choptank Paddle - 2026 - Sultana Education Foundation
Sat, May 16, 10:00 AM
Greensboro · Greensboro Boat Ramp in the Greensboro Community Park
Let The Prophets Speak
Fri, Apr 24, 6:00 PM
Saint Michaels · St. Michaels Inn
Let The Prophets Speak
Fri, Apr 24, 6:00 PM
Saint Michaels · St. Michaels Inn
5th Annual Paint Laurel Plein Air
Sat, May 9, 7:00 AM
Laurel · 500 Cooper St
5th Annual Paint Laurel Plein Air
Sat, May 9, 7:00 AM
Laurel · 500 Cooper St
Just added
MRPA Annual Golf Tournament
Tue, Apr 21, 9:00 AM
Cambridge · River Marsh Golf Club
Just added
MRPA Annual Golf Tournament
Tue, Apr 21, 9:00 AM
Cambridge · River Marsh Golf Club
Blackwater Public Paddle/Taylor's Is. - 2026 - Sultana Education Foundation
Sat, Jun 6, 10:00 AM
Cambridge · Blackwater NWR
Blackwater Public Paddle/Taylor's Is. - 2026 - Sultana Education Foundation
Sat, Jun 6, 10:00 AM
Cambridge · Blackwater NWR
Juneteenth in Caroline County For-Profit Vendor Registration
Fri, Jun 19, 11:00 AM
Preston · Mt. Pleasant Acres Farms
Juneteenth in Caroline County For-Profit Vendor Registration
Fri, Jun 19, 11:00 AM
Preston · Mt. Pleasant Acres Farms
A Night of Motown
Sat, Apr 18, 8:30 PM
Harrington · Gold Room
A Night of Motown
Sat, Apr 18, 8:30 PM
Harrington · Gold Room
Jesse Garron's Tribute to Elvis
Sat, Apr 25, 8:30 PM
Harrington · Gold Room
Jesse Garron's Tribute to Elvis
Sat, Apr 25, 8:30 PM
Harrington · Gold Room
The Kingsmen Dinner Concert
Fri, Apr 24, 6:00 PM
Harrington · Harrington Senior Center
The Kingsmen Dinner Concert
Fri, Apr 24, 6:00 PM
Harrington · Harrington Senior Center
Just added
Dinner and Comedy at the Nanticoke River Yacht Club
Sat, Apr 18, 5:00 PM
Seaford · Nanticoke River Yacht Club
Just added
Dinner and Comedy at the Nanticoke River Yacht Club
Sat, Apr 18, 5:00 PM
Seaford · Nanticoke River Yacht Club
Let's Hang On! America's #1 Frankie Valli Tribute
Sat, May 9, 8:30 PM
Harrington · Gold Room
Let's Hang On! America's #1 Frankie Valli Tribute
Sat, May 9, 8:30 PM
Harrington · Gold Room
Sales end soon
St. Michaels, Maryland Scavenger Hunt
Tomorrow at 11:00 AM + 429 more
Saint Michaels · Skipjack's St. Michaels
Sales end soon
St. Michaels, Maryland Scavenger Hunt
Tomorrow at 11:00 AM + 429 more
Saint Michaels · Skipjack's St. Michaels
Fall Fir Tree Foliage Public Paddle - 2026 - Sultana Education Foundation
Sat, Oct 17, 10:00 AM
Laurel · 201 Front St
Fall Fir Tree Foliage Public Paddle - 2026 - Sultana Education Foundation
Sat, Oct 17, 10:00 AM
Laurel · 201 Front St
Standup Comedy at Eastern Shore Brewing! (Saint Michaels, MD)
Sat, Apr 11, 7:00 PM + 1 more
Saint Michaels · Eastern Shore Brewing
Standup Comedy at Eastern Shore Brewing! (Saint Michaels, MD)
Sat, Apr 11, 7:00 PM + 1 more
Saint Michaels · Eastern Shore Brewing
Spring Wine Tasting - with Allie Balin
Tue, Apr 7, 5:30 PM
Saint Michaels · 209 N Talbot St
Spring Wine Tasting - with Allie Balin
Tue, Apr 7, 5:30 PM
Saint Michaels · 209 N Talbot St

Trends in Preston

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Frequently asked questions about Preston

What are the best events to attend?

According to Eventbrite, the best events are:

Mother’s Day Tea 2026 | Pouring Into Generations

Visit the Quaint Town of St. Michaels & Enjoy a Winery Tasting Tour

Turtle Paddle - 2026 - Sultana Education Foundation

Headwaters of the Choptank Paddle - 2026 - Sultana Education Foundation

Which events are currently trending in Preston?

The trending searches this month in Preston are:

motorcycle events

Which events are coming up?

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

St. Michaels, Maryland Scavenger Hunt

Realign: All-Inclusive 3-Day Women’s Retreat to Refresh & Recalibrate

Cookies With the Easter Bunny

Spring Wine Tasting - with Allie Balin