- 8 Nov2025Anna Wilson ft. Dave Weber @ The Blind Pig TavernThe Blind Pig Tavern | Savage, MD8pm-11pmSATURDAY
- 21 Nov2025Anna Wilson ft. Michael Neal (guitar) @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD4pm - 7pm FRIDAY
- 3 Jan2026Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 7 Feb2026Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 17 Feb2026Anna Wilson – Private EventOrlando, Florida
- 28 Feb2026Anna Wilson ft. Michael Neal (guitar) @ Island GreenIsland Green | Westminster, MD2pm - 5pm SATURDAY
- 7 Mar2026Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 4 Apr2026Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 2 May2026Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 6 Jun2026Anna Wilson ft. Dave Weber @ Sugarloaf MV (Drinking Buddies Event)Sugarloaf Mountain Vineyard | Dickerson, MD3pm-5pmSATURDAY
- 1 Aug2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 5 Sep2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 3 Oct2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 7 Nov2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 5 Dec2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
