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Arts & Entertainment, Community, Community Resources, Things to Do

Your Summer Festival Guide

June 29, 2026 by Piper Langenfeld

Summer in Maryland is packed with can’t-miss festivals, from parades and outdoor music to running events, crab feasts, and family-friendly fun. Whether you’re planning a weekend outing or filling your calendar for the season, here are the top festivals happening from July through September.

July Festivals You Can’t Miss

Dinner Under the Stars, July 1-September 30, West Street, Annapolis
Dine outdoors along West Street and experience live music, performances, and plenty of space to relax, dance, and enjoy the warm weather.

Annapolis Fourth of July Celebrations, July 3-4, Annapolis
Between a movie screening, festivals, family-friendly parades, live music, living history, and fireworks over Spa Creek, there is something for everyone on the Fourth of July in Annapolis!

First Sunday Arts Festival, July 5-November 1, West Street, Annapolis
Stroll down to West Street and shop from more than 100 vendors, enjoy live music and entertainment, and get delicious food from local restaurants. 

Additional July Festivals

Waugh Wednesdays, July 1-August 12, Waugh Chapel Towne Centre, Gambrills

Tides & Tunes Summer Concert Series, July 2-August 20, Annapolis Maritime Museum, Annapolis 

Summer Concerts, July 2-August 27, Annapolis Town Center, Annapolis

Naturalization Ceremony, July 3, William Paca House & Garden, Annapolis

Tunesday, July 7-September 1, Back Creek, Annapolis

Earleigh Heights Carnival, July 9-18, Earleigh Heights Fire Department, Severna Park

Plein Air Easton, July 10-19, Easton

Women’s Distance Festival 5K & Run After the Women 5K, July 11, West Annapolis Elementary School, Annapolis

River Days, July 11, Quiet Waters Park, Annapolis

Friends of Downs Park Concert Series, July 12-August 16, Downs Park, Pasadena

B.I.G. Book Sale, July 17-18 and August 28-29, Books for International Goodwill Warehouse, Annapolis

Illuminate Annapolis, July 18, Anne Arundel Community College, Arnold

Anchors & Artisans, July 19, August 16, September 20, and October 18, Annapolis Town Center, Annapolis

Banana Ball, July 31-August 1, Prince George’s Stadium, Bowie

August Festivals You Can’t Miss

Rotary Club of Annapolis Crab Feast, August 7, Navy-Marine Corps Memorial Stadium, Annapolis
Enjoy an all-you-can-eat feast with family and friends, a bake sale that could satisfy any sweet tooth, and lots of fun!

Made in Maryland Festival, August 16, Kurtz’s Beach, Pasadena
This family-friendly, Maryland-themed festival highlights all of the best offerings in our state. There will be live jousting, wine and beer, beautiful art, and so much more!

Maryland Renaissance Festival, August 29-October 25, Annapolis
Come dressed in your historical best and join in on the merriment! There will be fantastic performances, food stalls, and vendors upon vendors selling handmade products.

Additional August Festivals

Casey Cares 5K Run/One-Mile Walk, August 1, Maryland Zoo, Baltimore

Dog Days 8K Cross Country Run, August 2, Anne Arundel Community College, Arnold

Bags & Bravery Cornhole Tournament & Community Day, August 2, American Legion Post 175, Severna Park

A Taste of Arundel Grown, August 5, Homestead Gardens, Davidsonville

Puppy Plunge, August 23, YMCA Camp Letts, Edgewater

River Days, August 29, Annapolis Maritime Museum: Park Campus, Annapolis

Annapolis 10 Mile Run, August 30, Navy-Marine Corps Memorial Stadium, Annapolis 

September Festivals You Can’t Miss

Maryland Corn Maze, September-November, Gambrills
Take the whole family on an adventure through the corn maze and enjoy plenty of fun, themed nights. You can also enjoy farm games, meet some furry friends, and grab a pumpkin on the way out.

Annapolis Songwriters Festival, September 10-13, Annapolis
Inspired by the Key West Songwriters Festival, come see your favorite musicians on the big stage while surrounded by other music lovers!

Maryland Seafood Festival, September 12-13, Sandy Point State Park, Annapolis
Spend time with family, eat seafood to your heart’s content, shop around, and enjoy live music!

Annapolis Baygrass Music Festival, September 19-20, Sandy Point State Park, Annapolis
Listen to bluegrass and Americana jams by talented musicians across two stages and spend some time in the sand at Sandy Point State Park.

West Annapolis Oktoberfest, September 27, West Street, Annapolis
Enjoy the beer garden, sample food from local restaurants and food trucks, get ahead on holiday shopping, and spend time with family and friends on a late September day.

Additional September Festivals

September Sunset Concert Series, September 3-24, Annapolis Maritime Museum: Park Campus, Annapolis

Pops in the Park, September 5, Downs Park, Pasadena

Pops in the Park, September 6, Quiet Waters Park, Annapolis

River Days, September 12, Fort Smallwood Park, Pasadena

Kent Island Classic Pickleball Tournament, September 12-13, Mowbray Park, Stevensville

Bay Bridge Paddle, September 13, Sandy Point State Park, Annapolis

Ballet in the Garden, September 19, Hammond-Harwood House, Annapolis

Boatyard Beach Bash, September 19, Annapolis Maritime Museum: Park Campus, Annapolis

Annapolis RUN for the Light House, September 20, Quiet Waters Park, Annapolis

Blazers. Bourbon. Cigars, September 24, William Paca House & Garden, Annapolis

Fall Festival on the Green, September 26, Crofton Country Club, Crofton

Kunta Kinte Heritage Festival, September 26, Navy-Marine Corps Memorial Stadium, Annapolis

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Category: Arts & Entertainment, Community, Community Resources, Things to DoTag: Family Friendly, Festival, festivals See all posts by Piper Langenfeld

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