June in Annapolis & Anne Arundel County brings the season fully to life. With Anne Arundel Arts month activations, waterfront races, live music, Juneteenth celebrations, garden tours, and sunset sails. Here’s what’s happening this month. ⚓🎨☀️
Anne Arundel Arts Month 🎭
All Month Long
Anne Arundel Arts Month and Annapolis Arts Week brings exhibitions, performances, workshops, public art, and creative pop-ups across the county.
Pride Month 🌈
All Month Long
Although the parade and festival is in October 2026, there are plenty events to enjoy and celebrate Pride Month.
Paint Annapolis Plein Air Festival 🎨
May 31 - June 20, 2026
Downtown Annapolis becomes an open-air studio during Paint Annapolis. Artists set up throughout downtown to capture waterfront views and historic streets in real time.
Events include:
Santa Maria Cup ⛵
June 3-6, 2026
The Santa Maria Cup brings world-class women’s match racing back to the Severn River. Watch elite sailors compete in America’s Sailing Capital during one of Annapolis’ signature waterfront events.
Let’s Go! Music Festival 🎸
June 5-6, 2026
Let’s Go! Music Festival returns to the Anne Arundel County Fairgrounds with two days of high-energy performances, local flavor, and summer crowd energy.
This year’s lineup includes:
- Sublime
- AJR
- Fitz and the Tantrums
- Natasha Bedingfield
- & More!
Bring your crew, wear the comfortable shoes, and make a weekend of it.
Annapolis Juneteenth Parade & Festival ❤️💛💚
June 18-20, 2026
The Annapolis Juneteenth Parade & Festival celebrates freedom, heritage, Black culture, and community.
The weekend features:
- Downtown parade
- Live performances
- Local vendors
- Family-friendly activities
- Cultural programming throughout Annapolis
It’s one of June’s most meaningful community celebrations.
History, Heritage & Garden Experiences 🏛️
Throughout June
June brings plenty of ways to explore Annapolis and Anne Arundel County’s historic spaces, gardens, and stories.
Highlights include:
Waterfront Cruises, Paddles & Sailing ⛵
All Month Long
June belongs on the water. From sunrise paddles to sunset sails, the Chesapeake is calling.
On-the-water experiences include:
Farmers Markets, Makers & Local Finds 🧺
Recurring Throughout June
June weekends are made for browsing, snacking, and finding something local to take home.
Add these to your list:
Family-Friendly Fun 🌿
Throughout June
From garden stories to hands-on activities, June has plenty for families looking to get outside and explore.
Family-friendly picks include:
Music, Theater & Performances 🎤
Throughout June
Live music, theater, opera, and outdoor performances fill the calendar this month.
Don’t miss:
Father’s Day Weekend 👔
June 21, 2026
Celebrate Father’s Day with waterfront views, local flavor, and time outside.
Ideas include:
America 250 Experiences
Daily
The countdown to America’s 250th is underway, and Annapolis & Anne Arundel County are part of the story.
Explore:
Summer is officially settling in. Whether you’re here for the music, the water, the arts, or the history, June is the month to get out and make plans. Tag your adventures with @VisitAnnapolis or #VisitAnnapolis.
