It’s been awhile since we’ve had a Federal Holiday relieve us from our daily work duties, so the upcoming three-day weekend should provide a much-needed breather from all the usual chaos of life. At least, we hope it does.

If you don’t plan on spending three straight days sipping cocktails on a boat in the middle of the bay, or reading a book by the beach, or sleeping in and spending the weekend at home with family… If you must go out and do something in order to stay sane… Here’s what’s going on in Annapolis, and all over Maryland, on this Labor Day weekend. 

Maryland State Fair

Aug. 23 – Sept. 3, Lutherville-Timonium

The Maryland State Fair will be in full swing by the time Labor Day weekend hits, and it’s sure to go out with a bang. Jefferson Starship and Chris Jansen will be performing that weekend, exhibitors and vendors will line the fairgrounds and the usual delicious carnival concessions will be available. We’ll take a deep-fried everything, please.

Pops in the Park

Sept. 2, Annapolis

At this year’s annual Pops in the Park, the Annapolis Symphony Orchestra will fill Quiet Waters Park with the sound of classic film soundtracks from Titanic to Chicago to Superman. Pack a picnic dinner, lay out your blankets and lawn chairs and spend your Sunday evening listening to music in the park. 

Renaissance Festival

Aug. 25 – Oct. 21, Crownsville

What better way to celebrate Labor Day in Annapolis than at the 41st Maryland Renaissance Festival? Spend your weekend enjoying the 200+ entertainers, ten stages, a 3,000 seat jousting arena, 122 craft shops, 48 food and beverage emporiums, games and attractions of the 16th-century English village. The Festival will be open all weekend and on Labor Day Monday. 

Greenbelt Labor Day Festival

Aug. 31 – Sept. 3, Greenbelt

If you feel like venturing west, Greenbelt’s annual Labor Day Festival is celebrating its 64th year and will take place at Greenbelt’s Roosevelt Center. Festival-goers will find a wide range of activities and entertainment, including amusement rides and carnival games, live bands, food and refreshments, sports and recreation, art exhibits, art and photo show contests, a used book sale and a Labor Day Parade. 

Who’s at Rams Head?

Monday, 8/27: Donavon Frankenreiter w/ Ethan Tucker, Lisa Bouchelle

Tuesday, 8/28: Guitar Legend Dick Dale

Wednesday, 8/29: Joanne Shaw Taylor w/ JD Simo

Thursday, 8/30: Bob James

Friday, 8/31: The Classic Rock Experience feat. the music of Pink Floyd, Led Zeppelin, Styx, Boston, Deep Purple, Journey and more

Saturday, 9/1: Art Sherrod Jr. 

Sunday, 9/2: Secret Society

More information and details about these shows can be found here

Recurring Events

Dinner Under the Stars – Aug. 29, 6 – 10 p.m.

This summer, the Inner West Street Association is hosting a romantic evening event for families and friends under the stars. Spend a Wednesday night dining, dancing and listening to live bands in the middle of the street from 6pm to 10pm on the first block of West Street off Church Circle.  Participating restaurants will give you a wide choice of international and hometown flavors.

First Sunday Arts Festival — Sept. 2, 11 a.m. – 5 p.m.

The Arts Festival is held every Sunday from May 6th to November 4th on West Street in Downtown Annapolis. Shop from 130 local and regional artisans and enjoy outdoor cafes and more than seven live bands each day.  You can even explore galleries, take a game room challenge and even create your own artwork at shops on West Street.

Free Admission

Frederick Douglass Bicentennial Celebration- African American Experience Tour — Sept. 2, 1:30 – 3:30 p.m.

Colonial Tours of Annapolis is offering its new “African American Experience in Annapolis” walking tour every Sunday. Discover what life was like for all classes of African Americans in Annapolis, Anne Arundel County and Maryland from the colony’s founding in 1632 until the present day. The tour also shares Annapolis links to Frederick Douglass.

Exterior stops along the two-hour tour include: Banneker-Douglass Museum, Maynard Burgess House, William Butler House, Historic Annapolis Museum, Kunta Kinte Memorial and story wall, sites along Fleet and East Streets, Chase-Lloyd House, Hammond-Harwood House and the Thurgood Marshall Memorial.

Tours are offered Thursdays Fridays and Saturdays throughout the Summer. Check out the website for more information and to buy your ticket. http://www.colonialtoursannapolis.com

Sunday Outdoor Free Movies in the Garden – Sept. 2, 8:30 – 10:30 p.m.

First of all, who doesn’t love a Free Movie Screening? Add the fact that it is outside under the beautiful Annapolis sky, and you automatically have a family friendly, romantic, relaxed Sunday evening!

Every Sunday Night our Beer Garden becomes your Neighborhood Outdoor Movie Theatre with Free Classic Movie Screenings. All screenings are free and open to the public. Because all of our screenings begin at dusk, the start time may vary throughout the season.

Each Sunday we also feature a great Happy Hour from 3-7pm; come early and enjoy special features, and as the sun fades and movie starts, food and beverage service continues throughout the screening.

The cover image of this article is by Cristina on Flickr