SSM Summer Bucket List – Annapolis MD

The image features a tranquil marina with several sailboats docked. Clear skies and calm waters set a serene scene. Promotional content for a summer bucket list blog.

Welcome back and happy July!

We are so excited to head to Annapolis Maryland for all of the fun activities and events in July and beyond!

This image shows a lively street scene with people dining outdoors, colorful flags fluttering above, and a brick-lined pedestrian area flanked by leafy trees.
Image courtesy of Jeff Voigt Photography.

Wednesday, July 3, 5 p.m. – 10 p.m.

“Dinner Under the Stars: The first block of West Street in the heart of downtown Annapolis is closed to traffic on Wednesday evenings and select Saturday evenings in the summer and filled with tables reminiscent of the open-air cafes in France, Spain, and Italy. Enjoy an evening with family and friends under a canopy of white lights while enjoying live music and art demonstrations just ahead of the City’s July 4 festivities.” For more information head here! 


Street lined with American flags, illuminated by street lamps at dusk, with parked cars and a harbor in the background, evoking a patriotic atmosphere.

Image courtesy of

Thursday, July 4, 6:30 p.m. – 8 p.m.

“Join this patriotic salute to our nation with marching bands, old and new fire engines, cars and vans, service clubs, and scouts! ROUTE: The parade kicks off at Amos Garrett and West Street. We’ll head down West Street, the wrong way around Church Circle, and down Main Street. Anywhere along the parade route will provide a good view of the parade.” For more information head here. Our very own team member Pete will be in the parade!

Image courtesy of Bob Peterson.

Thursday, July 4, 8:00 pm – 9:15 pm (Fireworks begin at 9:15 pm)

“Annapolis launches its fireworks from a barge in Annapolis Harbor. Begin lining up at 8:00 PM for the best view. Viewing areas include public spaces Northeast of the Severn River, City Dock, along the Naval Academy Bridge (limited parking area), any of the street end parks facing Spa Creek, and aboard a boat in the Annapolis harbor. The Spa Creek Bridge will be closed to traffic from Eastport into Annapolis beginning at 6 p.m. The bridge will remain closed until the conclusion of the fireworks at approximately 10 p.m. Please be aware that the closer you get to downtown, the harder it will be to park and the more difficulty you will have getting out of town after the celebration. Click HERE for a list of parking options from the City of Annapolis.” For more information head here! 


A lively street festival with people browsing vendor tents under a clear sky. Colorful banners and a church spire rise in the background.

Image courtesy of Bob Peterson.

Sunday, July 7, 10 a.m. – 5 p.m.

“First Sunday Arts Festival: The Inner West Street Association is the proud sponsor of Maryland’s premier art festival. Held the first Sunday from May through November, thousands of visitors enjoy shopping along beautiful West Street in downtown historic Annapolis. Over 100 art/craft vendors, Café dining, and live entertainment to fill your afternoon. It’s the perfect weekend activity to kick off the July 4th weekend.”


Enjoy a summer sunset cruise.

“There is nothing like a summer sunset on the water. Enjoy dinner at one of the many incredible Annapolis restaurants, then climb on board for our 60-minute Annapolis Sunset Cruise. With a fun playlist, a full bar, and panoramic views, it is the perfect way to experience the sunset.

Similarly, we offer a 90-minute Annapolis Sunset Cruise with Live Music, featuring local musicians from many different genres. On Tuesday July 20th, we have a special 3-hour live music cruise with Caribbean Vibes Steel Drum Band: Caribbean Vibes on the Chesapeake. Check out all our live music cruises, here.”

Five Blue Angels jets, with "US NAVY" markings, are flying in tight formation against a light blue sky, demonstrating precision and teamwork.

Learn about the U.S. Naval Academy.

“Between our cruises and walking tours, we have a variety of ways to learn about the U.S. Naval Academy. For example, our 2.25-hour Colonial Annapolis & USNA Walking Tour will give you a wonderful introduction to Annapolis. Your period-attired guide will walk you through charming streets, the Maryland State House, and the U.S. Naval Academy as they share four centuries of history and culture.
During our 40-minute narrated Annapolis Harbor & USNA Cruise, you will learn the history of the Naval Academy, Annapolis’ role as a historic seaport, and the region’s waterways. (Plus, you will catch a glimpse of the Chesapeake Bay Bridge!) Similarly, our 40-minute narrated Spa Creek Cruise takes you along the banks of the Naval Academy in addition to the residential areas of Old Annapolis and Eastport.”


2024 Summer Concerts at City Dock


6/16/2024, 6/23/2024, 6/30/2024, 7/7/2024, 7/12/2024, 7/14/2024, 7/21/2024, 7/28/2024, 8/4/2024, 8/11/2024, 8/18/2024, 8/23/2024, 8/25/2024, 9/1/2024, 9/8/2024, 9/20/2024, 9/22/2024



A row of small, white sailboats, numbered 5 through 14, docked at a wooden pier bathed in warm sunset light with calm waters surrounding them.

See the Wednesday Night Sailboat Races Blow In

“In the mood for a little action? Head down near the Annapolis Yacht Club at 2 Compromise Street on a Wednesday summer night and you can catch the Wednesday Night Sailboat Races, a hugely popular tradition since 1967. This event will show you why Annapolis is called “America’s Sailing Capital.” Arrive by 6:00 p.m. and you’ll catch more than 100 sailboats getting ready for the races. There are hotels and restaurants along the waterfront like the Annapolis Waterfront Hotel that give you a front-row view of the races — or you could do one better and join in the races yourself on the Woodwind I or Woodwind II. It’s a quintessential Annapolis experience you’ll never forget.”


Experience Maryland State House Tours

“Once you’ve had your waterfront fill, you can walk up the hill to the Maryland State House, located on State Circle. You won’t miss this beautiful brick structure, as its dome is one of the most prominent features in the Annapolis skyline. It’s the oldest state capitol in continuous legislative use still in operation and the only one that can claim it was once used as the Nation’s capital, too. The Maryland State House offers self-guided tours that you can enjoy at your own pace, taking you through many historically important works of art and furniture. The building itself is open every day (except Christmas and New Year’s Day) and continues to be a vibrant part of the community and its history.”


Thank you for joining us! We will see you in August in Jacksonville!

Silverstreet Team

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