September is the very best time to be an Annapolis tourist. Here’s why.

People may think waterfront towns are just good for summer vacations, sipping cocktails on yachts, and crabbing off the dock, but Maryland’s summer heat can make enjoying all those things kinda hard. September in Annapolis is a Marylander’s answer to that problem. Here are nine reasons you should play tourist this month in Annapolis:

1. A Chesapeake Bay Boat Tour

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If you’ve never cruised the Bay in late summer or early fall, you’re in for a real treat. The sun shines just as bright, but without the oppressive heat and humidity — plus, that breeze off the water is just right for that stylish jacket you’ve been waiting to break out of your closet. Cruises on the Bay by Watermark offers several kinds of boat tours — from quick 40-minute tours of the harbor to full-day affairs!

2. Annapolis Walking Tours

If you’re looking for a day by the water, but aren’t a fan of boats, never fear! The same company that organizes the boat tours also does walking tours. There’s no better way to learn the history of Annapolis than to follow along with a tour guide dressed in period garb. And as September nears to an end, get into the October spirit with one of Watermark’s signature ghost tours.

3. The Rosé Terrace

Just like the tours listed above, the Rosé Terrace goes on all summer long, but ends after September. So if you haven’t made it over to Reynolds Tavern yet, go this Wednesday evening to see how they’ve decked out their courtyard in all things pink! Pink stringed lights twinkle overhead as you order from a menu filled with special pink wines and foods that pair perfectly with them. Great for date night or a girls’ night out!

4. Dinner Under the Stars

Now that the heat is beat, you can go to Dinner under the Stars (also a Wednesday event through mid-September) to enjoy dinner outdoors without sweating into your entree. West Street is closed down, so some of Annapolis’s tastiest restaurants can put tables out into the street so you can watch the sunset and do some stargazing while enjoying dinner.

5. Blazers, Bourbon, Cigars

September seems to be “festival month” for Annapolis, so there’s really no better time to pay a visit to the historic downtown. The William Paca House hosts their annual Blazers, Bourbon, Cigars fest on September 27 — a fine way to swill some of the best bourbon with the boys. Sorry, ladies, this is a gents-only event.

6. Twist and Stout Festival

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But the Twist and Stout Festival is fun for the whole family on Saturday, September 29! Set in Annapolis’s finest park, Quiet Waters, this festival brings together beer, wine, nature, and art. This one is definitely a September can’t-miss!

7. Kunta Kinte Heritage Festival

If you’re looking for something a little more educational, the 29th annual Kunta Kinte Festival is also on September 29 down by Annapolis City Dock. Alex Haley wrote about Kunta Kinte, one of 98 slaves brought to Annapolis, in his world-famous book Roots. Annapolis honors Kunta Kinte yearly in order to celebrate the progress people of color have made in America through their perseverance.

8. Annual Boatyard Beach Bash

And what about the Boatyard Beach Bash?! On September 15, come out and enjoy dinner from one of the best nautical restaurants on the Eastport side of Annapolis with some of the best local music. Summer won’t feel far off at this Jimmy Buffet-themed party. Proceeds go to the Annapolis Maritime Museum.

9. Annapolis Run for the Light House

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After talking up all these food and drink festivals, I should probably mention something healthy that Annapolis also makes a great setting for: exercise! The Annapolis Run for the Light House takes place on September 23 when the weather is nice and cool — no risk of overheating during this 5K! There is also the option of running a mile or five on a route that showcases some of the best scenery in town. Benefits go toward ending poverty and homelessness.

These are all events you can enjoy whether you’re an out-of-towner or if Annapolis is your own backyard. Don’t let September get forgotten between the end-of-summer blues and the build-up to Halloween. There’s something for everyone in this city.

Let me know what you’re looking forward to in the comments below!

Venture over to the Eastern Shore for the annual Alpaca Festival!

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