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7 Things To Do In Fall On The Eastern Shore

It’s the best kept secret on the Chesapeake Bay. A short burst of fall, filled with color changing leaves and crisp weather is an amazing time to explore Maryland’s Eastern shore. Here are seven things you must do in fall while visiting this beautiful destination.

There are some amazing things to do in Fall on the Eastern Shore. The crisp sweater-weather is lovely. The environment is bursting with colors. And it seems like the whole Eastern Shore is overflowing with fun. Don’t miss out on the short period after the oppressive heat moves out but before the frozen tundra takes over. Fall is amazing on the Eastern Shore.

For anyone who likes to be outdoors, this is the time to do it. From September to November the daily high temperatures can range from 84 degrees to 53 degrees. Humidity is generally low. On average, it rains about one day a month during this period. And since this is the low season for tourism in the area, you will find few crowds.

Take advantage of the best kept secret destination in the Fall: Maryland’s Eastern Shore!

Check out our favorite things to do in Fall on the Eastern Shore.

Photo Credit: Maryland Office of Tourism

7 Things To Do In Fall On The Eastern Shore

See the Fall foliage.

Fall is one of the best seasons on the Eastern shore because the oppressive heat of summer has passed, leading to crisp breezes and the most magnificent leaf colors you have ever seen.

Spend some time enjoying this short but magical season, with the brilliant crimson, gold, and canary colored leaves.

Take a scenic Sunday drive down a winding, country road, or head out in a boat to see the view from the water.

Take the time to enjoy it now because winter, with it’s cold and snow, will be here soon.

Enjoy the great outdoors (without the heat).

The much cooler weather in Fall means we can enjoy all of the outdoor activities we love without the heat and humidity that made them difficult during the summer.

You can paddle down the Manotokin River in a kayak or on a stand up paddle board.

Collect sea glass (and other treasures) walking the Chesapeake Bay shoreline or hit a few balls on nearby golf courses.

Hiking and biking are two more fun activities that are particularly well-suited for beautiful Autumn afternoons.

Have a campfire cookout.

Sure you can make s’mores and cook kabobs in the summer but sometimes the heat and bugs make it oppressive. That’s why Fall is the perfect time to get the fire started outdoors (weather and zoning permitted of course).

Why not try making your whole dinner over the campfire? Kids love it and there’s almost no clean up! Need some recipes? No problem. Check out some of our favorites here.

Take a ghost tour.

Maryland (and the entire Delmarva area) has spent nearly 400 years collecting restless spirits and the stories they have to tell. The scary stories of murder and mayhem are out there, just waiting to be uncovered...if you dare.

While Fall is traditionally the time people may think of taking a ghost tour, you can actually experience these ghastly adventures throughout the year. In fact, the Chesapeake Ghost Tours on the Eastern Shore boasts the largest trail of year round ghost tours in the entire country.

There are 11 “Ghost Walks” in a variety of historic towns, storytelling sessions, paranormal investigations and spooky bus tours all on Maryland’s Eastern Shore. The folklore which lingers from the region’s British and African heritage is something you can’t find anywhere else.

Have fun on the farm.

One of the best things to do in the Fall on the Eastern Shore is to have fun on the farm. There are many big farms which offer corn mazes, pumpkin patches, hayrides, petting zoos and outdoor activities galore.

It is so fun to celebrate fall on the farm! Smaller farms like Sugar Water Manor offer Fall activities too, such as harvesting vegetables, enjoying the animals and trying to spy the Bald Eagles that call the area home.


Who doesn’t love a good Oktoberfest? Brats, Bavarian pretzels and authentic German beer...oh my! While there are many great Oktoberfests around the country, going to one in Berlin, (Maryland) is especially fun. In addition to live German music, yummy German food, and even a reptile show, there’s something for everyone.

This year, Berlin’s Oktoberfest will be held on October 16, 2021. The event is free and there will be free parking too.

Tour a winery

If you thought you had to fly to France, Italy or California to experience a true winery, you were wrong! You can go vineyard hopping and taste some delicious wine right on the Eastern Shore.

Over the last few years, this area has evolved into one of the best places to go wine tasting on the East Coast (and maybe even the whole US)! Take a weekend to stroll through the beautiful vineyards and sample wines you didn’t even know existed!

You can follow the Chesapeake Wine Trail for some fun adventures.

These events and activities are sure to give you your fix of fun this Fall. Celebrate the fall harvest and the beauty of this short but wonderful season.

There are so many things to do in Fall on the Eastern Shore. Which one will you do first?



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