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Autumn Awaits in Annapolis, MD - My Favorite Fall Activites
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items Discover the best of fall in Annapolis with this list of activities that capture the season’s charm! From scenic drives and cozy cafés to local festivals and outdoor adventures, there’s something for everyone to enjoy. Experience the vibrant colors o...
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This is my go-to spot for cozy fall vibes! This local gem offers delicious, fresh food and drinks with a seasonal twist that perfectly captures autumn. Their Creme Brulee lattes are a must-try, and for the extra fall feel, I love getting a warm chai ...
Bean Rush Cafe
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Doepkens Farm in Gambrills has an incredible selection of pumpkins and flowers for your front porch decor, and the cutest kittens running around for perfect fall photo ops! Plus, they sell fresh farm eggs, so you can support local while picking up yo...
Doepkens' Farm
If you’re in the mood for a spooky good time, check out the Downtown Annapolis Ghost Tour! 👻 I always see the groups walking around with glow in the dark lanterns and it looks so much fun. The tour guides tell the haunted side of downtown Annapolis ...
Annapolis Ghost Tours & Crawls
Explore the trails and waterfront views while taking in the vibrant autumn colors. There are over 300 acres of trails, forests, and scenic waterfronts, it’s perfect for a cozy walk among changing leaves. Enjoy picnicking spots, a dog park for your fu...
Quiet Waters Park
If you're looking to unleash your creativity this fall, check out the seasonal classes at ArtFarm Annapolis! I have a wonderful personal connection to them and could not recommend them more—they take you in like the best friend you've had forever, al...
Fall Classes — ArtFarm - Classes, Events, Workshop, Rentals
A fantastic fall spot to enjoy fresh, local produce, artisanal goods, and seasonal treats. Open April-December, it features a diverse range of vendors offering everything from fruits and vegetables to handmade crafts and baked goods. It's the perfect...
Anne Arundel County Farmers' Market
I've heard so many great things about the afternoon tea at Reynolds Tavern within its charming historic venue. They serve a selection of teas with an assortment of freshly baked scones, pastries, and savory finger sandwiches. The elegant atmosphere a...
Reynolds Tavern
Even if you're not a big boat person, the annual boat show—both powerboats and sailboats—lasts just over a week, and the city is bustling, especially downtown. Admission is $25, and there’s so much to do! It’s a fantastic time of year when everyone c...
Annapolis Boat Shows
Take a day trip to drive along a scenic byway like the Chesapeake and Ohio Canal Scenic Byway or go for a hike through C&O Canal National Historic Park! DRIVE TIME: 6-8hrs - On a mix of country roads and state highways from Washington, D.C. to Cumberland, MD.
Scenic Byway - Chesapeake & Ohio Canal
Although this experience is on the pricier side, it’s definitely worth it for a special occasion or if you have the money to spend. You’ll make your way toward a bird’s-eye view of downtown Annapolis, then head back up the bay for a helicopter sights...
Annapolis Helicopter Tours | Charm Aviation Helicopters
The Annapolis Jazz & Roots Festival will be spread over the first two weekends of November in Historic Eastport. The festival brings international and regional performers to Maryland on the Chesapeake Bay. I have never been - but it seems fun! Ma...
Annapolis Jazz & Roots Festival
If driving isn't your thing, see the fall foliage in all its glory with a trip aboard the Western Maryland Scenic Railroad. Leaving from Cumberland, the three-hour train trip takes you through some of the most spectacular scenery while stopping off a...
Steam & Diesel Train Rides in Maryland — Western Maryland Scenic Railroad
The giant pumpkins are a local attraction for the public to visit and take photographs! They have been placed all around Annapolis, and although the main one is on Main St, here are the other locations: Annapolis Visitors Center, St. Anne's Episcopal...
GREAT ANNAPOLIS PUMPKINS