Trips & Adventurous Activities in Chesapeake

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

2026 Schock & Shivers Memorial 5k & Cold Water Challenge presented by Rogue Solar

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

Jon Langston

 Thu, 12 Mar at 11:00 pm Eagles Nest

Cookie Classic Run

 Sat, 17 Jan at 09:00 am 1246 Dismal Swamp Canal Trail

January - Mystery Cruise

 Sat, 24 Jan at 09:30 am Greenbrier Mall

Inner Alchemy Spiritual Day Retreat at The Holistic Treehouse - Chesapeake, VA

 Sat, 24 Jan at 12:00 pm The Holistic Treehouse

HeartStopper Haunted House Adventure!

 Fri, 13 Feb at 07:00 pm 1905 South Military Highway in Chesapeake Crossing Center, Chesapeake, VA

Awareness Hike Giveback Night at Wasserhund

 Wed, 04 Feb at 05:00 pm Wasserhund Brewing Company, 510 Belaire Ave, Chesapeake, VA 23320-4686, United States

Tidewater Striders | Distance Series #1

 Sat, 10 Jan at 08:30 am Rest Stop at Mile Post 4, Chesapeake Dismal Swamp Canal Trail Chesapeake, VA 23322 US

Valentine’s Day Mommi and mi

 Fri, 13 Feb at 10:00 am 444 St. Brides Rd W

OPEN HOUSE @ 1605 Tattinger Trail, Chesapeake, VA 23321

 Sat, 10 Jan at 12:00 pm 1605 Tattinger Trl, Chesapeake, VA 23321-1884, United States

🌉 South Norfolk Jordan Bridge + Paradise Creek Nature Park Walk (SNJB) 🌳

Sat, 07 Mar at 10:00 am 1400 Elizabeth River Way, Chesapeake, VA 23324

Just One More Loop! @ Oak Grove Lake Park 🌅🌳👟

Wed, 11 Mar at 06:00 pm Oak Grove Lake Park

Romp in the Swamp

 Sun, 08 Feb at 12:00 pm Dismal Swamp Canal Trail

Cross-Cultural Shamanic Medicine Wheel Training Shamanic Practitioner : A One Year Progam

 Sun, 11 Jan at 09:00 am The Holistic Treehouse

Mother’s Day Hike at Oak Grove Lake Park 💐🌿💗

Sun, 10 May at 08:00 am Oak Grove Lake Park

Tagalong 10K/Trefoil Trek 5K/Samoa Stroll 1 Miler/Do-Si-Don't Show Virtual 5K

 Sat, 17 Jan at 07:00 am Dismal Swamp Canal Trl, Chesapeake, VA 23322, United States

Self-Care City Scavenger Hunt – Based on Hot Habits Series: Chesapeake Area

 Thu, 03 Oct at 01:00 pm *Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED) USD 0 to 23