A local guide to the best things to do in Annapolis, Maryland, featuring City Dock, Ego Alley, Main Street, Quiet Waters Park, and the Chesapeake Bay waterfront.

The First Places I'd Take You in Annapolis, Maryland

July 12, 2026•2 min read

If you asked me where to spend a day in Annapolis, I wouldn't hand you a map—I’d show you the places that make this waterfront city so special.

As a local REALTOR®, I know that finding the right home is only part of the journey. Falling in love with the community is what truly makes a place feel like home.

Whether you're visiting for the first time or thinking about moving here, these are the places I'd recommend.

☕ Start with Coffee at Bean Rush Café or Curate Annapolis Café & Bakery

Every great day starts with a great cup of coffee. I love beginning the morning at Bean Rush Café or Curate Annapolis Café & Bakery, both local favorites with delicious coffee and pastries.

⚓ Visit City Dock & Watch the Yachts on Ego Alley

No visit to Annapolis is complete without stopping at City Dock. Take a stroll along the waterfront, watch the beautiful sailboats and yachts cruise through Ego Alley, and enjoy the lively atmosphere that makes downtown Annapolis so unique.

🏛 Tour the Maryland State House

Step into history at the Maryland State House, the oldest state capitol still in continuous legislative use. It's one of Annapolis' most iconic landmarks and a must-see for history lovers.

🛍 Explore Main Street

Spend some time walking along Main Street, where you'll find charming boutiques, art galleries, bookstores, gift shops, and locally owned businesses. It's the perfect place to shop and soak in the city's historic charm.

🌳 Relax at Quiet Waters Park

For a quieter escape, head to Quiet Waters Park. Enjoy scenic walking trails, waterfront views, picnic areas, public art, and beautiful green spaces just minutes from downtown.

🍽 Enjoy Fresh Seafood at Middleton Tavern or Iron Rooster

When it's time to eat, I always recommend Middleton Tavern for classic Annapolis seafood and waterfront history, or Iron Rooster for its famous comfort food and all-day breakfast.

🌅 End the Day Along the Chesapeake Bay

Before heading home, take one last walk along the waterfront and watch the sunset over the Chesapeake Bay. It's the perfect way to end a day in Maryland's capital city.

Why I Love Annapolis

Annapolis offers a unique blend of waterfront living, rich history, walkable streets, and locally owned businesses that make it one of Maryland's most desirable places to live and visit.

Whether you're searching for your next home or simply exploring the area, it's easy to see why so many people fall in love with Annapolis.

Thinking About Moving to Annapolis?

I'd love to help you find not just the right home, but the right community.

📖 I also offer FREE Maryland Buyer's Guides and Seller's Guides to help you navigate every step of your real estate journey.

Heather Taylor, GRI

I’m Heather Taylor, a Realtor® with RE/MAX One in Annapolis, Maryland, proudly serving buyers and sellers throughout Anne Arundel and Prince George’s Counties — including Annapolis, Crofton, Gambrills, Odenton, Davidsonville, Crownsville, Severn, Severna Park, Glen Burnie, Pasadena, Bowie, and beyond. Real estate is one of my greatest passions, and I dedicate the time, energy, and focus needed to ensure my clients always feel supported. My goal is to make every transaction as smooth and stress-free as possible while helping you achieve your real estate dreams. My clients know me for my calm, responsive guidance, deep local knowledge, and the personalized care I bring to every step of the process. Whether you’re relocating, downsizing, or making room to grow, I provide strategic, high-touch support tailored to your unique goals — never a one-size-fits-all approach. Relocation Downsizing with ease and confidence Upsizing and move-up strategies for growing families

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