- 30 May2025Anna Wilson & Dave Weber @ Black Ankle VineyardsBlack Ankle Vineyards | Mt. Airy, MD5pm-8pmFRIDAY
- 7 Jun2025Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD12pm-2pmSATURDAY
- 7 Jun2025Anna Wilson ft. Michael Neal (Guitar) @ Elks Lodge Music FestivalElk's Lodge | Winchester, VA5pm-6:30pmSATURDAY
- 21 Jun2025Anna Wilson (Private Event)Private Event2pm - 9pm SATURDAY
- 27 Jun2025Anna Wilson ft. Michael Neal (guitar) @ Maggie’sMaggie's | 310 E Green St, Westminster, MD7pm-10pmFRIDAY
- 28 Jun2025Anna Wilson ft. Michael Neal (Guitar) @ Frey’s Brewing Co.Frey's Brewing Co. | 8601 Mapleville Rd, Mt Airy, MD 217715pm-8pmSATURDAY
- 5 Jul2025Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 12 Jul2025Anna Wilson ft. Dave Weber @ Sagamore SpiritSagamore Spirit Distillery | Baltimore, MD1pm-4pmSATURDAY
- 26 Jul2025Anna Wilson ft. Michael Neal (Guitar) @ DTC Beer & WineDowntown Crown Beer & Wine7pm - 10pmSATURDAY
- 31 Jul2025Anna Wilson & Dave Weber @ Pike District Thursday’s in the ParkPike District | Grand Park Ave & Banneker Street | N. Bethesda 6pm-8pmTHURSDAY
- 8 Aug2025Anna Wilson @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD4pm - 7pmFRIDAY
- 30 Aug2025Anna Wilson ft. Dave Weber @ The Barn Resort Country Music FestThe Barn Resort | 75 Cunningham Rd, Gettysburg, PA 173251pm - 3pmSATURDAY
- 6 Sep2025Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
- 2 Oct2025Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD4pm - 7pmTHURSDAY
- 1 Nov2025Anna Wilson ft. Dave Weber @ Sugarloaf MVSugarloaf Mountain Vineyard | Dickerson, MD2pm - 5pm SATURDAY
