- 7 Mar2026Anna Wilson ft. Michael Neal @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 4 Apr2026Anna Wilson ft. Michael Neal @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 11 Apr2026Anna Wilson ft. Dave Weber @ Urbana LodgeUrbana Lodge | Urbana, MD7pm-10pmSATURDAY
- 19 Apr2026Anna Wilson ft. James Kirk @ Big Cork VineyardsBig Cork Vineyards | Rohrersville, MD1pm-4pmSUNDAY
- 2 May2026Anna Wilson ft. Michael Neal @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 29 May2026Anna Wilson ft. Dave Weber @ Windridge VineyardsWindridge Vineyards | Darnestown, MD5pm-8pmFRIDAY
- 6 Jun2026Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm-5pmSATURDAY
- 13 Jun2026Anna Wilson ft. Dave Weber @ The Blind Pig Tavern (Patio Party)The Bling Pig Tavern | Savage, MD6pm-9pmSATURDAY
- 20 Jun2026Anna Wilson ft. Dave Weber @ Kentlands Under the LightsKentlands, MarylandTBDSATURDAY
- 17 Jul2026Anna Wilson ft. Dave Weber (Private Event)Brunswick, MD6pm-9pmFRIDAY
- 1 Aug2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 2 Aug2026Anna Wilson ft. Dave Weber @ Big Cork VineyardsBig Cork Vineyards | Rohrersville, MD1pm-4pmSUNDAY
- 5 Sep2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 20 Sep2026Anna Wilson ft. James Kirk @ Big Cork VineyardsBig Cork Vineyards | Rohrersville, MD1pm-4pmSUNDAY
- 3 Oct2026Anna Wilson ft. TBD @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 16 Oct2026Anna Wilson ft. Dave Weber @ Urbana LodgeUrbana Lodge | Urbana, MD7pm-10pmFRIDAY
- 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
