Trips & Adventurous Activities in Chesapeake

Check out happening trips & adventurous activities events all around Chesapeake, VA

Girls United: Bergey’s Barnyard Visit

Sat, 04 Oct at 11:00 am Bergey's Barnyard

Fall Paddle

Sat, 11 Oct at 09:00 am 1224 Progressive Dr, Chesapeake, VA, United States, Virginia 23320

Pet Costume Contest at Historic Greenbrier Farms

Sat, 18 Oct at 10:00 am 225 Sign Pine Rd, Chesapeake, VA

D & D Adventures League

Fri, 17 Oct at 06:30 pm 469 N Battlefield Blvd, Chesapeake, VA, United States, Virginia 23320

The TBG Gathering of the Blacksmiths 2025

Sat, 25 Oct at 09:00 am 3300 Benefit Road, Chesapeake VA 23322

Hips of Horror 2025 RESERVED SEATING

Sat, 01 Nov at 06:30 pm TBD USD 23 to 28

Ricky Quinn at Triple R Ranch FALL

Sat, 15 Nov at 09:00 am Triple R Ranch

Fall Festival at Historic Greenbrier Farms

Tue, 30 Sep at 09:00 am 225 Sign Pine Rd, Chesapeake, VA

Costume Contest at Historic Greenbrier Farms

Sun, 26 Oct at 12:00 pm 225 Sign Pine Rd, Chesapeake, VA

Guided Kayak Tour/Lake Drummond via The Great Dismal Swamp Canal

Sat, 25 Oct at 09:00 am Dismal Swamp Canal Lake Drummond Launch

Oak Grove Lake Park Group Hike

Sat, 11 Oct at 10:00 am Oak Grove Lake Park

Horse Appreciation Day

Sat, 01 Nov at 01:00 pm 1246 Dismal Swamp Canal Trail

Dungeons & Dragons One-Shot Adventures at Big Ugly Brewing

Sat, 11 Oct at 12:00 pm Big Ugly Brewing

Cub Scout Joining Night

Tue, 30 Sep at 06:00 pm Edwin W Chittum Elementary School

Zombies at Ballahack

Sat, 25 Oct at 07:00 am 2900 ballahack rd, Chesapeake, VA, United States, Virginia 23322

2026 Schock & Shivers Memorial 5k & Cold Water Challenge

Sat, 24 Jan at 08:00 am Oak Grove Lake Park

REV

Sat, 13 Dec at 07:00 am 2900 ballahack rd, Chesapeake, VA, United States, Virginia 23322

Foodies + New Friends Chesapeake: Dinner with Strangers

Thu, 14 Aug at 07:00 pm Restaurant of the Week USD 34

SPOOKY STORY TIME! Foodies + Fears: Chesapeake | Dinner with Strangers

Mon, 01 Sep at 07:00 pm Restaurant of the Night USD 18

Adventurous Scavenger Hunt! - Great Bridge Galore Gander Hunt

Wed, 01 Jan at 08:00 am 100 Locks Rd USD 15