Best events in
Avenue

While the community is quiet, there is no shortage of events and things to do in Avenue, MD, with most of the action centered in nearby Leonardtown. As Southern Maryland's only Arts & Entertainment District, Leonardtown's walkable town square serves as the region's cultural heart. The area's character is deeply connected to the Chesapeake Bay, shaping everything from community festivals to the local food scene.

The social rhythm revolves around Leonardtown's historic town square, which comes alive with art and music during the monthly Monthly celebration.
Catch national and regional performers at The Rex Theatre, or find a more intimate acoustic set at a local spot like Olde Town Pub.
Enjoy outdoor entertainment with waterfront concerts at Leonardtown Wharf Park or weekend music and creative workshops at the Port of Leonardtown Winery.

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Nearby cities

Washington

47 miles away

Arlington

46 miles away

Alexandria

41 miles away

National Harbor

39 miles away

Fredericksburg

38 miles away

Waldorf

27 miles away

Springfield

42 miles away

Forestville

44 miles away

Bowie

48 miles away

Mitchellville

46 miles away

Quantico Base

34 miles away

Brock Hall

40 miles away

Neabsco

38 miles away

Hyattsville

49 miles away

Brandywine

30 miles away

Camp Springs

39 miles away

Merrifield

49 miles away

George Mason

49 miles away

Kingstowne

41 miles away

Mount Rainier

48 miles away

Falls Church

49 miles away

Cherry Hill

37 miles away

Brentwood

48 miles away

Lanham

49 miles away

Suitland

41 miles away

Westphalia

41 miles away

Rose Hill

41 miles away

Lake Ridge

41 miles away

Andrews AFB

40 miles away

Clinton

36 miles away

Washington

47 miles away

Arlington

46 miles away

Alexandria

41 miles away

National Harbor

39 miles away

Fredericksburg

38 miles away

Waldorf

27 miles away

Springfield

42 miles away

Forestville

44 miles away

Bowie

48 miles away

Mitchellville

46 miles away

Quantico Base

34 miles away

Brock Hall

40 miles away

Neabsco

38 miles away

Hyattsville

49 miles away

Brandywine

30 miles away

Camp Springs

39 miles away

Merrifield

49 miles away

George Mason

49 miles away

Kingstowne

41 miles away

Mount Rainier

48 miles away

Falls Church

49 miles away

Cherry Hill

37 miles away

Brentwood

48 miles away

Lanham

49 miles away

Suitland

41 miles away

Westphalia

41 miles away

Rose Hill

41 miles away

Lake Ridge

41 miles away

Andrews AFB

40 miles away

Clinton

36 miles away

Online Events

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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Wed, Nov 18 • 10:00 AM CST

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Fri, Nov 20 • 8:00 AM CST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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The 1911 Triangle Shirtwaist Factory Fire in NY - Film History Livestream

Sat, Mar 13 • 3:00 PM EST

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thursday • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

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Virtual - Powerful Gottman Method Couples Therapy Tools

Fri, Nov 20 • 8:00 AM CST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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The 1911 Triangle Shirtwaist Factory Fire in NY - Film History Livestream

Sat, Mar 13 • 3:00 PM EST

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Events near Avenue

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Northern Neck Sound Bath

Tomorrow • 5:00 PM

CB Creative Arts Center

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AFCEA Dahlgren - Small Business Speaker Series

Wednesday • 8:30 AM

Kitty Hawk Technologies

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Boots & BBQ Hoedown

Sat, Nov 7 • 4:00 PM

Greenwell State Park

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So MD Smooth Steppaz "Fall In Line" Field Party

Sat, Nov 7 • 3:00 PM

Knight Life Ball Field (formerly Jolly Gents/Stardust/Kitchen Latrice)

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Watercolor Blooms Painting Party

Tue, Nov 10 • 5:00 PM

22694 Washington St

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SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)

Sat, Nov 14 • 7:00 PM

22725 Duke St

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Vendor or Sponsor Registration for Home for The Holidays

Sat, Dec 5 • 4:00 PM

Saint Mary's Fairgrounds

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Sotterley Garden Guild Wreath Workshop

Sat, Dec 5 • 9:00 AM

Historic Sotterley

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Northern Neck Sound Bath

Tomorrow • 5:00 PM

CB Creative Arts Center

Check ticket price on event

AFCEA Dahlgren - Small Business Speaker Series

Wednesday • 8:30 AM

Kitty Hawk Technologies

Check ticket price on event

Boots & BBQ Hoedown

Sat, Nov 7 • 4:00 PM

Greenwell State Park

Check ticket price on event

So MD Smooth Steppaz "Fall In Line" Field Party

Sat, Nov 7 • 3:00 PM

Knight Life Ball Field (formerly Jolly Gents/Stardust/Kitchen Latrice)

Check ticket price on event

Watercolor Blooms Painting Party

Tue, Nov 10 • 5:00 PM

22694 Washington St

Check ticket price on event

SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)

Sat, Nov 14 • 7:00 PM

22725 Duke St

Check ticket price on event

Vendor or Sponsor Registration for Home for The Holidays

Sat, Dec 5 • 4:00 PM

Saint Mary's Fairgrounds

Check ticket price on event

Sotterley Garden Guild Wreath Workshop

Sat, Dec 5 • 9:00 AM

Historic Sotterley

Check ticket price on event

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Frequently asked questions about Avenue

Where are the best spots for live music events near Avenue?

The Rex Theatre in Leonardtown is a top venue for musical events and touring acts. For a more casual setting, Port of Leonardtown Winery hosts musicians nearly every weekend, and Olde Town Pub features regular acoustic performances.

What are some good date night ideas in the Leonardtown area?

A great date night could involve a show at The Rex Theatre or a tasting at Port of Leonardtown Winery. For a more scenic evening, consider a waterfront dinner on Solomons Island or taking one of the sunset cruises from the Leonardtown Wharf.

Are there any family-friendly events or activities in the area?

Historic St. Mary's City offers outdoor educational experiences and seasonal festivals perfect for families. Leonardtown Wharf Park is also a great spot for community events and enjoying the waterfront, with space for picnics and recreation.

What kind of art and culture events happen around Leonardtown?

Leonardtown's Arts & Entertainment District is centered around the monthly Monthly event. Galleries and shops extend their hours, and the town square comes alive with performances. Port of Leonardtown Winery also hosts creative workshops like painting nights.

How can I find free things to do near Avenue, MD?

Strolling through Leonardtown's historic Town Square is a great free activity, especially during the monthly Monthly celebration. You can also enjoy the scenery at Leonardtown Wharf Park or explore the waterside trails at Historic St. Mary's City.

What is the food and drink scene like in the Avenue and Leonardtown area?

The local scene emphasizes waterfront dining and local producers, with a focus on Chesapeake Bay seafood. Port of Leonardtown Winery is a community hub for local wine, while Brudergarten offers craft beer in a German-style beer garden setting.

Is there much nightlife near Avenue?

The region's nightlife is relaxed and centered on live music and social gatherings rather than clubs. Brudergarten, inside Shepherd's Old Field Market, hosts regular trivia and karaoke nights. Olde Town Pub and the winery are also popular evening spots.

Which outdoor activities are popular in the area?

Kayaking and paddleboarding from Leonardtown Wharf Park are very popular on Breton Bay. For a major outdoor event, the annual U.S. Oyster Festival celebrates the region's tidewater culture, and the park sometimes hosts seasonal outdoor concerts.