Every summer, Annapolis becomes the busiest hub for boating in the Chesapeake Bay. With tons of creeks, rivers, sandbars, and little islands to explore, you’ll truly never be bored or running out of new places to go. Pier 7 Marina is located on the South River, just a quick sail from Downtown Annapolis, and the perfect place to call your home base for the season. The lineup of events in the area is something you don’t want to miss. From floating concerts to firework shows, Annapolis has something for everyone this boating season.
All Summer Long
Tunesday on the Water
Every Tuesday evening through August, local musicians perform live from a floating stage on Harness Creek. Anchor up, pour a drink, and enjoy one of the most unique summer concert experiences in the Bay.
Wednesday Night Races
A tradition in Annapolis sailing, the Annapolis Yacht Club’s Wednesday Night Races take place weekly through the summer. Even if you’re not racing, they’re fun to watch from your boat or from the waterfront restaurants downtown.
Tides & Tunes Summer Concert Series
Hosted by the Annapolis Maritime Museum, this waterfront concert series brings live music to the docks every Thursday evening. It’s a casual, bring-your-chair kind of event perfect for summer nights.
Chesapeake Cowboys Boat Docking Competitions
These high-speed docking contests are one of the most entertaining things you’ll see on the water. Skilled captains race to squeeze their workboats into impossibly tight slips at top speed, usually to the roar of a big crowd. Their current schedule is as follows:
- East Riverfest in Mathews, VA: July 5th
- Cape Charles, VA: August 4th
- St. Michaels, MD: August 11th
- Pocomoke, MD: August 17th
- Crisfield, MD: September 1st
- Salisbury, MD: September 7th
- Hoopers Island, MD: September 8th
- Solomons Island, MD: September 15th
- Chincoteague, VA: September 28th
June
Summer Solstice Sunset Paddle – June 20
Kick off the official start of summer with a peaceful group paddle on Back Creek. This sunset event begins around 6:30pm and is a great way to soak in the longest day of the year.
Eastport a Rockin’ – June 28
This local favorite brings dozens of bands to multiple outdoor stages in the maritime neighborhood of Eastport. Grab a ticket, walk (or dinghy) over from Pier 7, and enjoy a full day of great music, local food, and waterfront views.
July
Round Bay Fireworks – July 3
The fireworks show over Round Bay is a local secret and happens the night before the main Annapolis celebration. It’s a great option for boaters who want a more relaxed, family-style fireworks experience.
Annapolis July 4th Parade & Fireworks – July 4
Annapolis goes all out for the Fourth of July. The day starts with a patriotic parade through the heart of town and ends with a fireworks show over the harbor, best viewed from the water.
Solomons Island Fourth of July Boat Parade – July 4
A bit farther south, this colorful parade on the water is a festive way to celebrate Independence Day. Boats of all shapes and sizes dress up in red, white, and blue for a patriotic cruise through the harbor.
August
Annapolis Crab Feast – August 1
Held at the Navy-Marine Corps Memorial Stadium from 5 – 8pm, this all-you-can-eat crab feast is one of the largest in the country. Come hungry, this event is a rite of passage for locals and visitors alike.
Pirate Weekend in Rock Hall – August 8 – 10
Just across the Bay, Rock Hall transforms into a pirate’s paradise for one weekend every summer. Expect dinghy races, costume contests, and plenty of rum-fueled fun. It’s a quirky, can’t-miss event for cruisers.
September
Big Band Night in St. Michaels – Labor Day Weekend
Wrap up the season with one of the Eastern Shore’s most charming events. Big Band Night features live swing music, dancing under the stars, and a fireworks finale over the Miles River.
Labor Day Weekend – August 30 – September 1
Labor Day marks the unofficial end of boating season, and there’s no better way to send it off than with a long weekend of raft-ups, boat days, and marina cookouts.
Whether you’re here for a night, a month, or the whole season, there’s always something happening around the Bay. Pier 7 Marina keeps you close to all the action while offering a peaceful place to unwind between adventures. Come see why summer in Annapolis is best experienced by boat!