Sailing events near Annapolis, MD

Wed, May 7 · 3:00 PM UTC

Day Sail Wednesday after Cinco

The New Annapolis Sailors Club • Annapolis, MD

Group name:The New Annapolis Sailors Club

Annapolis, MD

SOS Annapolis Happy Hour

Singles on Sailboats • Annapolis, MD

Group name:Singles on Sailboats

Annapolis, MD

SOS Kent Island Happy Hour

Singles on Sailboats • Annapolis, MD

Group name:Singles on Sailboats

Annapolis, MD

Sat, May 17 · 3:00 PM UTC

Cross Island Trail (Kent Island) + Optional "Beach Hopping"

MD Rail Trail Biking • Silver Spring, MD

Group name:MD Rail Trail Biking

Silver Spring, MD

Thu, May 8 · 10:00 PM UTC

Pirates of the North (PON) Paddles - Jean Roberts Park, Havre de Grace

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Sat, May 10 · 1:00 PM UTC

Paddle from Jonas Greene Park to Sandy Point, and return

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Wed, May 7 · 8:00 PM UTC

Season Opener: Arundell -Jonas & Catharine Green Park beach

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Sat, May 10 · 2:00 PM UTC

Kent Island Ramble Bicycle Ride

Washington Women Outdoors • Washington, DC

Group name:Washington Women Outdoors

Washington, DC

Wed, May 21 · 8:00 PM UTC

🏴‍☠️ Pirates of Arundell: Homeport Farm Park + WHEELS + gate code

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Wed, May 14 · 8:00 PM UTC

🏴‍☠️Pirates of Arundell: Exploring Galesville & Shady Side creeks

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Sat, May 10 · 3:00 PM UTC

Let’s Paddleboard/Kayak Back Creek Annapolis - Must Have Own Equipment

Howard County Social Club • Columbia, MD

Group name:Howard County Social Club

Columbia, MD

Wed, May 14 · 8:30 PM UTC

Happy Hour at the Chart House - Wednesday Night Boat Races

Little Bit of Everything (LBE) • Annapolis, MD

Group name:Little Bit of Everything (LBE)

Annapolis, MD

Sat, May 10 · 3:00 PM UTC

Paddleboard/Kayak Back Creek-Must have your own equipment.

Little Bit of Everything (LBE) • Annapolis, MD

Group name:Little Bit of Everything (LBE)

Annapolis, MD

Sat, May 17 · 12:30 PM UTC

2025 Kent Island Paddle Series (KIP)

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Wed, May 14 · 10:00 PM UTC

MID-WEEK Easy Goin' Communal Paddle, Solley's Cove, Wed 5/14 !

The WatersEdge Kayak Club, Baltimore's Sea-Kayaking Club! • Baltimore, MD

Group name:The WatersEdge Kayak Club, Baltimore's Sea-Kayaking Club!

Baltimore, MD

Sat, May 10 · 3:00 PM UTC

Let’s Paddleboard/Kayak Back Creek Annapolis-Must Have Own Equipment.

Charm City Social Club • Baltimore, MD

Group name:Charm City Social Club

Baltimore, MD

Monday Edgewater Social Paddle

Maryland SUP and Kayak Meet-Up Tortilla FLOtilla • Annapolis, MD

Group name:Maryland SUP and Kayak Meet-Up Tortilla FLOtilla

Annapolis, MD

Fri, May 16 · 9:30 PM UTC

Friday Night Social @ Green Gaven Wharf

Maryland SUP and Kayak Meet-Up Tortilla FLOtilla • Annapolis, MD

Group name:Maryland SUP and Kayak Meet-Up Tortilla FLOtilla

Annapolis, MD

Wed, May 14 · 10:45 AM UTC

Pimlico Sunrise Tour

Photo Society MD/VA/DC • Annapolis, MD

Group name:Photo Society MD/VA/DC

Annapolis, MD

Sat, May 24 · 12:45 PM UTC

Eastern Neck Tim Dole Memorial Paddle

Chesapeake Paddlers Association • Annapolis, MD

Group name:Chesapeake Paddlers Association

Annapolis, MD

Sat, May 10 · 2:30 PM UTC

Marley Creek Paddle with Lunch at Ram's Head Dockside

Wicked Fun Kayakers • Columbia, MD

Group name:Wicked Fun Kayakers

Columbia, MD