Summer is arriving in full swing around Annapolis ☀️ From waterfront art shows and outdoor dining to community festivals and family-friendly celebrations, June is full of ways to enjoy the season and spend time around the local community.



Paint Annapolis

May 31st - June 7th

As summer starts settling into Annapolis, Paint Annapolis brings artists and the community together in one of the most scenic spots around 🎨 From waterfront views to live painting events, this week-long tradition is a great excuse to stroll through town and enjoy the creative energy of the season.

Paint the Town





Dinner Under the Stars

Recurring Wednesdays Throughout Summer

Warm evenings, outdoor dining, and live entertainment make Dinner Under the Stars one of the best ways to enjoy summer in Annapolis ✨ Whether you are meeting up with friends or planning a casual night out, the atmosphere makes every Wednesday feel like a mini summer getaway.

Dine Under the Stars




CAC’s 13th Annual Chip in for the Arts Golf Tournament

June 10th

Nothing pairs better with summer weather than a day on the golf course ⛳ This annual tournament combines friendly competition, community support, and local arts advocacy for a fun event that gives back while bringing people together.

Support the Arts





Third Annual Summer Fest

June 13th

Summer Fest is all about kicking off the season with live entertainment, local vendors, and community fun ☀️ With activities for all ages and a lively atmosphere, it is the kind of event that makes summer weekends in Annapolis feel special.

Kick off the Summer


Annapolis Juneteenth Celebration

June 20th

The Annapolis Juneteenth Celebration is a meaningful day of community, culture, and celebration ❤️ From live performances and local vendors to educational experiences and family activities, this event brings people together while honoring an important part of history.

Celebrate!





Father’s Day Bash

June 21st

Looking for a fun way to celebrate Father’s Day weekend? 🎉 The Father’s Day Bash is packed with summer energy, good food, entertainment, and activities the whole family can enjoy together along the waterfront.

Dine with Dad