3-Day Fall Nature Adventure in Maryland

Day 1: Annapolis Exploration

Annapolis, Maryland

8:00AM

Breakfast at Chick & Ruth's Delly

Start your day with their famous crab omelet or the classic pancakes, fueling up for a day of exploration.
Head to the first destination by walking or driving around the historic downtown area.
USD20, 1 hour

9:30AM

Visit Sandy Point State Park

After breakfast, spend the morning soaking in the vast views of the Chesapeake Bay, with beautiful fall colors starting to emerge.
Drive 15 minutes to Sandy Point State Park.
USD5 Entry Fee, 2 hours

12:00PM

Lunch at the Boathouse Bistro

Enjoy a waterfront lunch featuring fresh regional seafood while taking in the marina views.
Head back to Annapolis for lunch, it's a short 20-minute drive.
USD40, 1.5 hours

1:30PM

Historic City Dock Walk

Take a leisurely stroll around the City Dock, enjoying the fall foliage and local shops along the waterfront.
This is within walking distance from the Boathouse Bistro.
Free, 1 hour

2:30PM

Sailing on the Chesapeake Bay

Book a scenic sailing tour in the afternoon to experience the beautiful fall weather and stunning bay views.
Several sailing tours depart from the City Dock area.
USD65, 2 hours

5:00PM

Dinner at O’Leary’s Seafood

Savor a delicious dinner featuring local crab cakes and seasonal sides to end the day on a high note.
Head to O’Leary’s, a short 15-minute walk from the City Dock.
USD50, 1.5 hours
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Day 2: Patapsco Valley State Park

Patapsco Valley State Park, Maryland

8:00AM

Breakfast at The Iron Rooster

Indulge in their famous rooster biscuits and breakfast hash before setting off to the park.
Drive 30 minutes to the restaurant.
USD25, 1 hour

9:30AM

Hiking at Patapsco Valley State Park

Embark on one of the park's scenic trails, where you’ll witness vibrant fall foliage around every turn.
Drive 20 minutes to the park entrance after breakfast.
Free, 3 hours

1:00PM

Picnic Lunch in the Park

Pack a picnic with sandwiches and snacks to enjoy at a scenic overlook inside the park.
Find a picnic area within the park.
USD15, 1 hour

2:00PM

Visit the Thomas Viaduct

Check out this historic railroad bridge, offering picturesque views perfect for photography.
Drive to the Thomas Viaduct area, a 15-minute drive in the park.
Free, 1 hour

3:00PM

Mountain Biking

Grab a bike and hit the trails for an exhilarating ride in the park with stunning views along the way.
Bike rentals are available nearby or bring your own.
USD30 for rentals, 2 hours

5:30PM

Dinner at The Park Grill

Wind down your day with a hearty dinner featuring farm-to-table dishes inspired by local flavors.
Drive 10 minutes to The Park Grill.
USD60, 1.5 hours
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Day 3: Assateague Island Adventure

Assateague Island, Maryland

8:00AM

Breakfast at the Donut Connection

Start with some fresh, hand-crafted donuts and coffee - a perfect pick-me-up for your day of adventure.
Drive 90 minutes to Assateague Island.
USD20, 1 hour

9:30AM

Wildlife Viewing on Assateague Island

Spend the morning exploring the island's unique ecosystems and observing the famous wild ponies roaming free.
Head into the park from the entrance of Assateague Island.
USD20 Park Fee, 2 hours

11:30AM

Kayaking in the Bay

Rent a kayak and paddle through the calm waters while enjoying breathtaking views of the island’s landscape.
Look for rentals nearby or pack your own gear.
USD35, 2 hours

2:00PM

Lunch at Assateague Island National Seashore Visitor Center

Grab a light lunch at the visitor center; they offer snacks and regional specialties.
Backtrack to the Visitor Center for lunch.
USD25, 1 hour

3:00PM

Beach Time at Assateague

Spend your afternoon on the pristine beach, collecting shells and enjoying the sun as you relax.
Head straight to the beach area from the Visitor Center.
Free, 3 hours

6:30PM

Dinner at The Island Creamery

End your adventure with delicious homemade ice cream and a savory dinner in this charming spot as a sweet closure to your trip.
Take a short drive from the beach to the creamery.
USD30, 1.5 hours
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