Trips & Adventurous Activities in Winchester

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

Farm Concert - CAZHMIERE at West Oaks!

 Fri, 15 Aug at 07:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Farm Concert - Souled Out at West Oaks!

 Fri, 19 Sep at 07:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Bones Owen at The Monument

 Sat, 30 Aug The Monument

2025 Winchester Greek Festival

Sat, 16 Aug at 11:00 am 1700 Amherst St, Winchester, VA, United States, Virginia 22601

TalkWalk Community Walks - August

 Mon, 18 Aug at 06:00 pm 1 N Loudoun St Free

A Christmas Carol

 Thu, 06 Nov at 07:00 pm Winchester Little Theatre

Jess’s Crochet Craftings Class

Sat, 16 Aug at 01:00 pm 125 S. Loudoun Street, Winchester, VA

WCM Community Picnic

 Sun, 07 Sep at 12:00 pm Willow Grove Farm Free

3rd Annual Alumni Picnic!

 Sat, 13 Sep at 12:00 pm Kiwanis Club II Pavilion | 812 Oak Drive , Winchester, VA 22601

TalkWalk Community Walks - September

 Mon, 15 Sep at 06:00 pm 1 N Loudoun St Free

Adventures Through Grief - Winchester Teen Group

 Mon, 11 Aug at 05:00 pm 314 Hope Dr, Winchester, VA 22601-6800, United States

Campout at “Winning at Winchester”

 Fri, 29 Aug at 05:00 pm Church of Christ at Mountain View

Phelpsmore Farm Stone Soup Gathering

 Thu, 04 Sep at 11:00 am 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

TalkWalk Community Walks - October

 Mon, 20 Oct at 06:00 pm 1 N Loudoun St Free

SUP YOGA 1/2 Day Immersion

 Sun, 17 Aug at 09:00 am Winchester Va

Superpalooza 2025

 Sat, 20 Sep at 08:00 am 351 Victory Road, Winchester, VA, United States, Virginia 22602

Holy Cannoli: A Tour of Italian Sweets

 Sun, 07 Sep at 02:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

The Lowdown Drifters at The Monument

 Sun, 05 Oct The Monument

Adventures Through Grief - Winchester Young Adult Group

 Wed, 27 Aug at 05:30 pm Handley Regional Library System

3-DAY RIDE!!!

 Sat, 30 Aug at 08:30 am Farmers Livestock Exchange, Inc.

A Christmas Carol at Winchester Little Theatre Inc.

 Fri, 07 Nov at 08:00 pm Winchester Little Theatre Inc.

MSV at Night: The Lua Project

 Fri, 26 Sep at 05:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

GORUCK LIGHT CHALLENGE (CADRE DAN INAUGURAL RIDE)

 Mon, 18 Aug at 06:00 pm Winchester Recreation Center, 1001 War Memorial Dr, Winchester, VA 22601, USA

Saving Abel

 Wed, 15 Oct at 07:00 pm Backseat Events

Awesome Scavenger Hunt - Winchester Wonders

 Tue, 19 Nov at 08:00 am 12 N Cameron St USD 15