Best events in
Highland Beach

With a rhythm set by the Chesapeake Bay sailing season, there are many events and things to do in and around Highland Beach, MD. The area's social calendar is shaped by a lively maritime culture and the historic, walkable streets of nearby Annapolis. From major annual boat shows to intimate performances in the Arts District, the scene offers a dynamic mix of large-scale festivals and local gatherings.

Evenings in downtown Annapolis often involve strolling between historic pubs and waterfront restaurants before settling in for a show at a venue like Rams Head On Stage.
The Annapolis Arts District is a hub for creativity, hosting the monthly Monthly Arts Festival and featuring nightly performances at cozy spots like 49 West Coffeehouse.
Warmer months bring unique local traditions to life, including popular midweek sailboat races on the water and al fresco dining events that close down streets for the evening.

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National Harbor

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Bowie

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McLean

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Laurel

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Vienna

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Waldorf

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Fair Oaks

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Events near Highland Beach

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2026 Fall Craft Fair

Saturday • 10:00 AM

Chesapeake High School

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Stan & Joe's Saloon

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11/16- Annapolis, MD- Friendsgiving in Wine Country

Mon, Nov 16 • 7:00 PM

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Manhattan Beach Holiday Market Vendor Registration

Thu, Dec 3 • 6:00 PM

Manhattan Beach Clubhouse

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Mini Birth Class

Sat, Dec 12 • 9:00 AM

AAMC - Clatanoff Pavilion

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Talent Machine Presents Holiday Spectacular 2026: Frosty Follies

Sun, Dec 20 • 11:00 AM

Arundel High School

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Sun, Jan 24 • 7:30 PM

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Ballet Theatre of Maryland presents "Coppélia"

Fri, Apr 23 • 7:30 PM

Maryland Hall

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2026 Fall Craft Fair

Saturday • 10:00 AM

Chesapeake High School

Check ticket price on event

Laughs in the Lounge

Saturday • 7:00 PM

Stan & Joe's Saloon

Check ticket price on event

11/16- Annapolis, MD- Friendsgiving in Wine Country

Mon, Nov 16 • 7:00 PM

Cooper’s Hawk Winery & Restaurant

Check ticket price on event

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Thu, Dec 3 • 6:00 PM

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Check ticket price on event

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Sat, Dec 12 • 9:00 AM

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Check ticket price on event

Talent Machine Presents Holiday Spectacular 2026: Frosty Follies

Sun, Dec 20 • 11:00 AM

Arundel High School

Check ticket price on event

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Sun, Jan 24 • 7:30 PM

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Frequently asked questions about Highland Beach

Where can I find live music events near Highland Beach?

Rams Head On Stage hosts national touring musicians in an intimate setting. For a more casual vibe, The Admiral's Cup on the Annapolis waterfront has live music daily, and 49 West Coffeehouse in the Arts District is known for jazz and folk performances.

What are some art-focused events in the Annapolis Arts District?

The Annapolis Arts District is packed with galleries and creative events. A popular recurring event is the Monthly Arts Festival, a street fair held monthly from May through November featuring artisan vendors and performers. Maryland Hall also hosts a variety of arts programming.

What's a good plan for a date night that includes an event?

A classic date night can involve seeing a show at the Classic Theatre of Maryland. The walkable downtown area also offers many pubs and restaurants along the water, perfect for before or after your event. For something different, consider a monthly cabaret performance.

Are there popular outdoor events in the area?

The waterfront is central to many outdoor events in the Annapolis area. The annual in-water boat shows are major draws in the spring and fall, and weekly sailboat races are a beloved local spectacle during warmer months. You can also find outdoor musicals.

How can my family find kid-friendly activities?

The Maryland Renaissance Festival, held on fall weekends just outside Annapolis, is a great family outing. The Anne Arundel County Farmers' Market is another good option, offering local goods in a relaxed atmosphere on Saturdays and Sundays year-round.

What are some free things to do around Annapolis?

Many community activities are free to attend, though vendors may charge for goods. Strolling through the Monthly Arts Festival is free, as is watching the weekly sailboat races from the shoreline. Exploring the historic City Dock area is always a great free option.

Where's the best neighborhood for nightlife events?

The historic downtown and City Dock area is the center of Annapolis nightlife. The neighborhood is very walkable, with numerous pubs and waterfront taverns like The Admiral's Cup that feature live music events and stay open late, especially on weekends.

Does the area have any unique food and drink events?

Yes, the Dinner Under the Stars series is a popular weekly tradition. From May through September, part of West Street in the Arts District closes for a large, festive outdoor dining event with live music and a great community atmosphere.

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Nearby cities

Washington

Baltimore

Arlington

Alexandria

Columbia

Silver Spring

College Park

Reston

Fairfax

Towson

Tysons Corner

Bethesda

Annapolis

North Bethesda

Rockville

Gaithersburg

Pleasant Hills

National Harbor

Crownsville

Glen Burnie

Bowie

Bel Air South

McLean

Laurel

Vienna

Catonsville

Waldorf

Konterra

Fair Oaks

Germantown

Washington

Baltimore

Arlington

Alexandria

Columbia

Silver Spring

College Park

Reston

Fairfax

Towson

Tysons Corner

Bethesda

Annapolis

North Bethesda

Rockville

Gaithersburg

Pleasant Hills

National Harbor

Crownsville

Glen Burnie

Bowie

Bel Air South

McLean

Laurel

Vienna

Catonsville

Waldorf

Konterra

Fair Oaks

Germantown

Online Events

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