Main Street
Annapolis's Main Street offers a picturesque journey through history with charming red-brick buildings, unique shops, and harbor views.
Highlights
Must-see attractions
Social
From TikTok & Reddit
Best Time
Fewer crowds, peaceful exploration
Main Street
Best Time
Fewer crowds, peaceful exploration
Highlights
Must-see attractions
Annapolis's Main Street offers a picturesque journey through history with charming red-brick buildings, unique shops, and harbor views.
"Wander through charming streets lined with red-brick buildings, unique shops, and historic architecture."
🦀 Crab Cake Pretzel Must-Try
Don't miss the famous crab cake pretzel at Davis Pub for a unique local flavor!
📚 Bookworms' Paradise
Explore Old Fox Books and Coffee for a cozy reading nook and a great selection of books.
Highlights
Discover the most iconic attractions and experiences
Historic Main Street Stroll
Downtown Annapolis
Wander through charming streets lined with red-brick buildings, unique shops, and historic architecture.
Annapolis City Dock
End of Main Street
Enjoy picturesque harbor views, watch boats, and soak in the lively atmosphere of this waterfront hub.
Maryland State House
State Circle
Explore the oldest US state capitol in continuous legislative use, offering a glimpse into American history.
Plans like a pro.
Thinks like you
Planning Your Visit
Timing Your Visit to Main Street
Navigating Annapolis's Charm
Best Times
Insider Tips
from TikTok, Instagram & Reddit
🦀 Crab Cake Pretzel Must-Try
Don't miss the famous crab cake pretzel at Davis Pub for a unique local flavor!
📚 Bookworms' Paradise
Explore Old Fox Books and Coffee for a cozy reading nook and a great selection of books.
🛍️ Naptown Flea Market
Check out the Naptown Flea for vintage finds and local crafts on select Sundays. +1
👟 Comfortable Walking Shoes
You'll be doing a lot of walking, so pack comfy shoes to explore the historic streets.
Tips
from all over the internet
🦀 Crab Cake Pretzel Must-Try
Don't miss the famous crab cake pretzel at Davis Pub for a unique local flavor!
📚 Bookworms' Paradise
Explore Old Fox Books and Coffee for a cozy reading nook and a great selection of books.
🛍️ Naptown Flea Market
Check out the Naptown Flea for vintage finds and local crafts on select Sundays. +1
👟 Comfortable Walking Shoes
You'll be doing a lot of walking, so pack comfy shoes to explore the historic streets.
🌅 Sunset Cruise Magic
Experience a magical sunset cruise with live music for a romantic evening.
What Travellers Say
Reviews Summary
Visitors consistently praise Annapolis's charming historic streets, picturesque waterfront, and delicious seafood, especially the famous crab cakes. The city's walkable nature and abundance of unique shops make it a delightful destination. Some find parking challenging during peak times, and certain areas can get crowded.
What People Like
What People Dislike
Frequently Asked Questions
🚇 🗺️ Getting There
Main Street is easily accessible by car, with several parking garages nearby. For a convenient option, consider the Annapolis Circulator bus, which stops at key locations.
Yes, there are parking garages such as the Noah Hillman Garage and the Gott's Court Garage. Arriving early is recommended, especially on weekends.
While it's a scenic drive of about 45 minutes to an hour from D.C., walking is not feasible. Consider it a great day trip destination.
Many of Annapolis's attractions, including Main Street, are walkable. The Annapolis Circulator bus is also a great way to get around without a car.
The drive to Annapolis itself can be quite scenic, especially as you approach the Chesapeake Bay. Enjoy the journey!
🎫 🎫 Tickets & Entry
No, walking down Main Street and exploring the shops is free. Some attractions within the area may have admission fees.
Shop hours can vary, but most are open from late morning to early evening. It's best to check individual store hours if you have specific places in mind.
While strolling Main Street is free, sites like the Maryland State House may have specific visiting hours and potential tour fees.
Events like the Naptown Flea Market may require vendor fees or have free admission. Check event listings for details. +1
The Annapolis City Dock is a public area and is free to visit. Enjoy the waterfront views and atmosphere.
🍽️ 🍽️ Food & Dining
Annapolis is famous for its crab cakes! Don't miss the crab cake pretzel at Davis Pub or the offerings at Chick & Ruth's Delly.
While specific restaurants on Main Street vary, the area is known for its seafood. Consider exploring nearby Eastport for highly-rated spots like Vin 909. +1
Yes, Old Fox Books and Coffee is a popular spot for both books and coffee, offering a charming atmosphere.
Chick & Ruth's Delly is a classic choice for casual eats and deli-style fare.
Many restaurants offer diverse menus. It's always a good idea to check menus online or ask your server about vegetarian and vegan choices.
📸 📸 Photography
Capture the historic red-brick architecture, charming storefronts, and the picturesque Annapolis City Dock. The Maryland State House also offers great photo opportunities. +1
Golden hour, just after sunrise or before sunset, offers beautiful lighting for capturing the street's charm. Evenings can be magical with the lights.
Consider a sunset cruise for stunning harbor photos or capture the vibrant atmosphere of the Naptown Flea Market. +1
Photography policies can vary inside historic buildings. It's best to check with the venue directly or look for posted signage.
A versatile lens like a 24-70mm is great for capturing both street scenes and details. A wide-angle lens can be useful for architecture.
For Different Travelers
Tailored advice for your travel style
👨👩👧 Families with Kids
🚶♀️ Solo Travelers & Day-Trippers
💑 Couples & Romantic Getaways
Deep Dives
In-depth insights and expert knowledge
Exploring Annapolis's Historic Charm
Beyond the shops, the proximity to the Annapolis City Dock provides stunning waterfront views and a lively atmosphere. Here, you can watch boats, enjoy the sea breeze, and soak in the maritime heritage of the city. The Maryland State House, located nearby at State Circle, is another significant historical landmark, being the oldest state capitol in continuous legislative use.
For those interested in local culture and community, events like the Naptown Flea Market offer a chance to browse vintage items and support local vendors.
Culinary Delights of Annapolis
For seafood lovers, exploring the eateries in areas like Eastport, adjacent to Main Street, is highly recommended. Restaurants such as Vin 909 have garnered significant praise for their culinary offerings, including steak appetizers and creative dishes.
Beyond seafood, visitors can find charming spots like Old Fox Books and Coffee, which serves as a cozy cafe for a relaxing break.
Social
from TikTok, Instagram & Reddit