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Best events in
Shady Side

For events and things to do in Shady Side, MD, the local scene is rooted in its quiet, waterfront community spirit. Life moves at a slower pace, with many gatherings centered on Chesapeake Bay heritage and outdoor activities. While the area offers a peaceful escape, residents often travel to nearby Galesville for dockside dining or Annapolis for a wider array of cultural attractions.

For a casual bite and local music, many head to the neighboring village of Galesville to enjoy the atmosphere at waterfront spots like Pirate's Cove.
Community life often revolves around the Shady Side Community Center and the historic Captain Avery Museum, which hosts workshops and concerts on the water.
Annual traditions mark the calendar, including the Galesville Maritime Heritage Festival in the fall and community parades celebrating local heritage.

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Prince George's County Forestry Board's Tree Tour primary image

Prince George's County Forestry Board's Tree Tour

Sat, Oct 17 • 9:00 AM

Tree Tour

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Ghouls Just Wanna Have Fun : Campfire Experience

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Montpelier Farms

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Mini Birth Class

Sat, Oct 17 • 10:00 AM

AAMC - Clatanoff Pavilion

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10/20-Annapolis, MD- Dinner After Dark

Tue, Oct 20 • 7:00 PM

Cooper’s Hawk Winery & Restaurant

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Family Fishing & Crabbing Day at the Patuxent River primary image

Family Fishing & Crabbing Day at the Patuxent River

Sat, Oct 24 • 10:00 AM

Patuxent Riverkeeper

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The Masquerade Affair Presented by DJ Prez & DJ Kelly Kellz primary image

The Masquerade Affair Presented by DJ Prez & DJ Kelly Kellz

Sat, Oct 31 • 6:00 PM

Oak Creek Golf Club

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PlanetTyrus Tour Jan. 24th Annapolis, MD primary image

PlanetTyrus Tour Jan. 24th Annapolis, MD

Sun, Jan 24 • 7:30 PM

DoubleTree by Hilton Hotel Annapolis

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Ballet Theatre of Maryland presents "Coppélia" primary image

Ballet Theatre of Maryland presents "Coppélia"

Fri, Apr 23 • 7:30 PM

Maryland Hall

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Prince George's County Forestry Board's Tree Tour primary image

Prince George's County Forestry Board's Tree Tour

Sat, Oct 17 • 9:00 AM

Tree Tour

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Ghouls Just Wanna Have Fun : Campfire Experience primary image

Ghouls Just Wanna Have Fun : Campfire Experience

Sat, Oct 17 • 4:00 PM

Montpelier Farms

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Mini Birth Class primary image

Mini Birth Class

Sat, Oct 17 • 10:00 AM

AAMC - Clatanoff Pavilion

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10/20-Annapolis, MD- Dinner After Dark primary image

10/20-Annapolis, MD- Dinner After Dark

Tue, Oct 20 • 7:00 PM

Cooper’s Hawk Winery & Restaurant

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Family Fishing & Crabbing Day at the Patuxent River primary image

Family Fishing & Crabbing Day at the Patuxent River

Sat, Oct 24 • 10:00 AM

Patuxent Riverkeeper

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The Masquerade Affair Presented by DJ Prez & DJ Kelly Kellz primary image

The Masquerade Affair Presented by DJ Prez & DJ Kelly Kellz

Sat, Oct 31 • 6:00 PM

Oak Creek Golf Club

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PlanetTyrus Tour Jan. 24th Annapolis, MD primary image

PlanetTyrus Tour Jan. 24th Annapolis, MD

Sun, Jan 24 • 7:30 PM

DoubleTree by Hilton Hotel Annapolis

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Ballet Theatre of Maryland presents "Coppélia" primary image

Ballet Theatre of Maryland presents "Coppélia"

Fri, Apr 23 • 7:30 PM

Maryland Hall

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Nearby cities

Washington

28 miles away

Baltimore

33 miles away

Arlington

31 miles away

Alexandria

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31 miles away

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30 miles away

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35 miles away

Reston

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Annapolis

10 miles away

Fairfax

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38 miles away

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Bethesda

33 miles away

Crownsville

11 miles away

Gaithersburg

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Bowie

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Catonsville

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Rockville

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National Harbor

27 miles away

Laurel

26 miles away

Glen Burnie

23 miles away

Waldorf

26 miles away

Vienna

40 miles away

Bel Air South

46 miles away

McLean

37 miles away

Springfield

36 miles away

Konterra

27 miles away

Potomac

38 miles away

Germantown

47 miles away

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33 miles away

Arlington

31 miles away

Alexandria

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Columbia

31 miles away

Silver Spring

30 miles away

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35 miles away

Reston

46 miles away

Annapolis

10 miles away

Fairfax

43 miles away

College Park

26 miles away

Tysons Corner

38 miles away

Towson

40 miles away

Bethesda

33 miles away

Crownsville

11 miles away

Gaithersburg

42 miles away

Bowie

15 miles away

Catonsville

33 miles away

Rockville

39 miles away

National Harbor

27 miles away

Laurel

26 miles away

Glen Burnie

23 miles away

Waldorf

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40 miles away

Bel Air South

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McLean

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Springfield

36 miles away

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38 miles away

Germantown

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Washington Crossing the Delaware / The Crossing - Film History Livestream

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HBR Book Webinar: Resilient Optimism

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(ONLINE) Women on the Move with Ann Patchett

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No Title, No Permission, No Problem: Harnessing the Power of Influence primary image

No Title, No Permission, No Problem: Harnessing the Power of Influence

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The MI5 Archive: Official Secrets

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Shady Side

What are some family-friendly events in the Shady Side area?

The region offers several annual events perfect for all ages. Look for the Galesville Maritime Heritage Festival in the fall and community parades. The Captain Avery Museum also hosts educational programs with a focus on Chesapeake Bay culture for the whole family.

Where can I find live music events near Shady Side?

Most live music is found at casual, waterfront venues in nearby Galesville. Places like Pirate's Cove often feature local musicians. For larger concerts and a bigger selection of venues, residents typically drive thirty minutes to Annapolis.

Are there any food and drink events in Shady Side?

Yes, the area hosts community-focused culinary gatherings. The Galesville Heritage Society puts on an Annual Soup & Chili Cook Off each September. Local dock bars in the neighboring village of Galesville also provide a hub for casual dining and drinks by the water.

What is the nightlife like in Shady Side, MD?

Nightlife in Shady Side is very relaxed and low-key. The social scene centers on local community gatherings or casual evenings at dock bars in Galesville. For more active nightlife with more bars and clubs, Annapolis is the primary destination.

How can I find free events to attend in Shady Side?

Many community events in the area are free to attend. The annual Fourth of July parade is a popular free event for residents. Exploring local parks like Franklin Point State Park is another great way to enjoy the area without cost.

What kind of outdoor events happen in the Shady Side area?

Outdoor life centers on the Chesapeake Bay with boating and fishing. Community events often have an outdoor component, like the Galesville Maritime Heritage Festival. The annual Turkey Shoots at the Shady Side Community Center also offer a unique local outdoor activity.

Where's a good place for art and culture events in Shady Side?

The Captain Avery Museum is the main hub for local culture and art events. It hosts workshops and programs celebrating the region's maritime heritage. The Maryland Day Celebration Weekend each March also highlights local history at various sites.

What's the event scene like in the neighboring village of Galesville?

Galesville serves as a social hub for Shady Side residents, offering more dining options. Its scene is built around waterfront restaurants and community halls like the Galesville Memorial Hall. The village hosts several annual events, including its own parade and a maritime festival.