Leonardtown Festival Guide 2025 | Find Culture & Street Fairs In Leonardtown

Q: What are the upcoming Festivals in Leonardtown?

Here are the upcoming events in Leonardtown: U.S. Oyster Festival, Live at the Oyster Festival, Chesapeake Mermaid at U.S. Oyster Festival, Veteran's Day Celebration, Ace’s Angels Breast Cancer Awareness Walk & Pink Soiree

Q: Which kind of events are trending in Leonardtown?

Here are the top trending events in LeonardtownFestivals, 🎃 Halloween, Trunk Or Treat, Live Music, Car Shows

Festivals in Leonardtown

Sat, 18 Oct

U.S. Oyster Festival

St. Mary's County Fairgrounds
Sat, 18 Oct

Live at the Oyster Festival

St Marys County Fairgrounds
18-19 Oct

Chesapeake Mermaid at U.S. Oyster Festival

St. Mary's County Fairgrounds
Tue, 11 Nov

Veteran's Day Celebration

Town Market LLC
Sat, 25 Oct

Ace’s Angels Breast Cancer Awareness Walk & Pink Soiree

Leonardtown Wharf

Festivals from nearby cities

Most talked

Sat, 01 Nov

Dupont Circle Halloween Bar Fest 2025

Dupont Circle

22+ Interested

|

USD 5
Sat, 11 Apr

Lemon Festival 2026

Cultural Enrichment Center

186+ Interested

|

Free
21-22 Mar

An All Pink Affair

TBA

|

Free
Sat, 29 Aug

Cultural Enrichment, Music, and Arts Festival

Laurel Park

21+ Interested

|

Free
Sun, 19 Oct

WILDERNESS HALLOWEEN FESTIVAL & CAR SHOW

Wilderness Presidential Resort, Plank Road, Spotsylvania Courthouse, VA, USA

18+ Interested

|

Free
11-12 Apr

LEMONFEST 2026

Cultural Enrichment Center

26+ Interested
Sat, 25 Oct

PATAWOMECK HALLOWEEN FESTIVAL

Patawomeck Museum & Cultural Center

17+ Interested

|

Free
31 Oct-01 Nov

DC Halloween Party Cruise | Titanic Masquerade

Spirit of Washington DC by Hornblower

36+ Interested
Sat, 18 Oct

LOVEPAWS Adoption Event at RA Howl-O-Ween Festival

Browns Chapel Road

Frequently Asked Questions

Which Festivals can I attend in Leonardtown this weekend?

Here are the best Festivals happening in Leonardtown this weekend:

U.S. Oyster Festival is happening on Sat 18 Oct 2025 from 10:00 AM onwards at St. Mary's County Fairgrounds, Leonardtown
Live at the Oyster Festival is happening on Sat 18 Oct 2025 from 4:00 PM onwards at St Marys County Fairgrounds, Leonardtown
Chesapeake Mermaid at U.S. Oyster Festival is happening on Sat 18 Oct 2025 from 12:00 PM onwards at St. Mary's County Fairgrounds, Leonardtown

What are the upcoming Festivals in Leonardtown?

Here are the upcoming Festivals in Leonardtown:

U.S. Oyster Festival is happening on Sat 18 Oct 2025 from 10:00 AM onwards at St. Mary's County Fairgrounds, Leonardtown
Live at the Oyster Festival is happening on Sat 18 Oct 2025 from 4:00 PM onwards at St Marys County Fairgrounds, Leonardtown
Chesapeake Mermaid at U.S. Oyster Festival is happening on Sat 18 Oct 2025 from 12:00 PM onwards at St. Mary's County Fairgrounds, Leonardtown
Veteran's Day Celebration is happening on Tue 11 Nov 2025 from 9:00 AM onwards at Town Market LLC, Leonardtown
Ace’s Angels Breast Cancer Awareness Walk & Pink Soiree is happening on Sat 25 Oct 2025 from 8:00 AM onwards at Leonardtown Wharf

Which kind of events are trending in Leonardtown?