Maryland’s 15 Best Tours & Things To Do: Which To Choose?

Maryland is a surprisingly diverse state when it comes to things to do. You might come for the Chesapeake Bay’s seafood and end up paddleboarding, or explore historic Civil War sites and stumble upon a lively wine tour. The local charm combines scenic landscapes, rich history, and small-group adventures that feel authentic and well-curated.

For instance, the Assateague Island Cruise offers a rare chance to see the island’s famous wild ponies from the water—an experience you won’t want to miss if nature is your thing.

Or if you prefer something lively, the Axe-Throwing activity in Columbia promises a fun, competitive twist to your trip where you can learn a new skill and enjoy some self-serve drinks.

Maryland’s best tours provide a mix of outdoor fun, cultural exploration, and engaging storytelling—perfect for all interests.

Quick Overview

This list covers a broad range of tours and activities, from adventure sports like axe-throwing and kayaking to historic battlefield visits and culinary tours. Whether you’re into wildlife watching, wine tasting, or self-guided scavenger hunts, Maryland has something to suit your pace.

For a peaceful sunset cruise, or a hands-on horseback ride, check out the options below, each with solid reviews and unique features. Now, let’s dive into what makes each experience stand out.

1. Axe-Throwing

At number 1 on our list, Axe-Throwing in Columbia is a perfect way to try something new while having a blast. For just $38.41 per person, you get about two hours of friendly competition in a private group—max 15 people.

The setup is casual, with guests pouring their own wine or beer (self-serve), adding a relaxed, social vibe. You’ll learn the proper technique and challenge your friends to see who hits the bullseye first.

It’s ideal for small parties, bachelor/bachelorette groups, or anyone looking to add a little excitement to their trip. The activity’s high rating (5.0/5 from 39 reviews) speaks to its fun, approachable environment.

Bottom Line: If you want a fun, slightly unconventional activity that combines skill, friendly rivalry, and self-guided drinks, axe-throwing offers a memorable couple of hours. Just be prepared for some sore arms the next day!

2. Assateague Island Cruise Departs from Ocean Pines

Number 2 on our list, the Assateague Island Cruise, is a must-do for wildlife lovers. The 2-hour boat trip from the Ocean Pines Yacht Club ($40.00 per person) takes you down the Assawoman Bay to see the island’s famous wild ponies up close. The trip is highly rated (5.0/5 from 22 reviews), thanks to knowledgeable captains like Frank and Bryce who share insights about the area’s ecology and history.

The boat navigates around the island’s backside, offering a different perspective than the usual land-based views. Kids and adults alike enjoy spotting dolphins, birds, and the ponies grazing along the shoreline.

This tour is perfect if you want a relaxed, scenic escape that combines nature, wildlife, and local stories. The boat’s intimate atmosphere and informative narration make it stand out from larger, generic cruises.

Bottom Line: For about two hours immersed in the beauty of Assateague’s wildlife, this cruise balances fun and education beautifully. Great for families and nature enthusiasts.

3. Bicycle Rental from Visitor Center location at Assateague

Number 3 offers a simple, active way to explore Assateague Island: bicycle rental for around $12.00 per person. The 6 miles of protected bike paths make it easy to see the island’s beaches, marshes, and wild horses at your own pace.

Many reviewers mention how accessible and safe the trails are, with some sightings of horses right on the beach or on the bay side. Since there’s no entrance fee when entering by bike, it’s an affordable way to get some exercise and enjoy nature.

If you prefer a more independent experience than a guided tour, renting bikes provides freedom and flexibility. Guides or maps help you navigate, and you can stop whenever a photo opportunity or a wild horse grazing presents itself.

Bottom Line: Renting a bike on Assateague is an excellent option for those seeking a self-paced, scenic adventure with plenty of chances to encounter wildlife. Just remember to bring your camera.

4. Guided Assateague Kayaking and Wildlife Discovery Tour

Number 4 is the Guided Kayaking Tour, perfect for hands-on explorers interested in marine life and birdwatching. For $75.00, this 2.5-hour trip takes you through salt marshes and along the island’s shores, focusing on wildlife sightings like crabs, mussels, and—of course—the wild horses.

Expert guides lead you safely through the waters, sharing insights into the ecosystem and helping you spot various species.

This tour is especially memorable because it offers a more intimate experience with nature than a boat cruise. It’s suited for beginners and experienced paddlers alike, with tandem or single kayaks available. The reviews praise the guide Brice for his knowledge, and many mention how close they got to seeing the wild horses.

Bottom Line: If you want a participatory experience that combines sport and nature, kayaking on Assateague offers a memorable adventure with expert guidance.

5. Berlin Tasting Tour: A Delicious Walk Through History

Number 5 stands out as a culinary journey through the charming town of Berlin, Maryland. Costing $110 per person, this 3-hour walking tour takes you along Main Street, where you’ll sample treats from local restaurants and specialty shops.

Along the way, you’ll learn about the families behind the town’s development and see sights where Hollywood filmed the movie “Runaway Bride.” The tour blends food, history, and architecture, with guests discovering why Berlin was named the “Coolest Small Town in America.”

The tour offers a laid-back pace, making it suitable for foodies and history buffs alike. With reviews highlighting the fun and tasty experience, it’s a great way to explore Maryland’s culinary scene and small-town charm.

Bottom Line: For a relaxed, tasty day exploring historic Berlin, this tour combines culture and cuisine in a delightful way.

6. Single Sit on Top Kayak Rental at Assateague Island, MD

Number 6 offers a solo kayaking experience for about $38.00 per person. Paddle along the serene waters of Sinepuxent Bay and enjoy the solitude of the island’s natural beauty.

The rentals are ideal for those comfortable on the water and looking for a peaceful way to see Assateague’s marshes and wildlife. Many reviews mention how the calm bay makes for an easy paddle, with chances to spot ospreys and other birds overhead.

This activity suits independent travelers who want to customize their own adventure without a guide. It’s perfect for a half-day escape into nature, with the flexibility to explore at your own pace.

Bottom Line: Solo kayaking on Assateague is a peaceful option for confident paddlers wanting a personalized nature experience.

7. Harborside Orange Crush Cruise

Number 7 is the Harborside Orange Crush Cruise, a lively way to see the bay for $45.00 per person. The cruise includes a free orange crush cocktail when you order lunch from Harborside Bar, making it a popular social outing.

The boat heads toward Assateague Island, with views of wild ponies, dolphins, and the Chesapeake scenery. The reviews praise the knowledgeable captain Kathy and the friendly atmosphere.

Ideal for casual travelers who want a fun, social experience with drinks and scenic views, this cruise combines sightseeing and relaxation with a bit of local flavor.

Bottom Line: If you’re looking for a relaxed, social cruise with good drinks and wildlife views, this tour is a top pick.

8. Horseback Riding Through Scenic Park in Brookeville

Number 8 offers a private horseback riding experience, perfect for those who want a personal touch. For $300 per group (up to 2 people), your 1.5-hour ride takes you through lush landscapes and scenic trails. Guests rave about the beautiful scenery and the well-trained, personable horses.

The location’s peaceful setting allows for a quiet, contemplative experience, especially suited for beginners or anyone craving a gentle ride.

The guide’s attention to individual needs makes this a special, tailored activity. It’s a great fit for a romantic outing or a solo adventure in nature.

Bottom Line: Private horseback riding in Brookeville offers a memorable, serene encounter with Maryland’s countryside—ideal for couples or solo adventurers.

9. Self-Guided Scavenger Hunt: The Fine (Art) Life in Bethesda

Number 9 combines technology with sightseeing. For just $12.31, you get a digital scavenger hunt through Bethesda using the Let’s Roam app. You’ll visit key locations, complete challenges, answer trivia, and take digital photos along the way.

This activity is perfect for small groups or families who enjoy exploring at their own pace and want an interactive way to see the city’s art, architecture, and culture.

Many reviews mention how fun and engaging the experience is, especially with the personalized roles and team options. It’s a flexible way to learn about Bethesda’s local art scene and hidden corners.

Bottom Line: For a budget-friendly, interactive day of discovery, this self-guided hunt offers a personalized adventure through Bethesda’s streets.

10. South Mountain Private Battlefield Tour

Number 10 is a private Civil War battlefield tour led by historian Dr. Brad Gottfried. For $120 per group (up to 5), the 3-hour experience covers key sites like Gathland State Park and the battles of South Mountain. Dr. Gottfried’s 45 years of teaching and authoring books on the Civil War bring history vividly to life.

The tour includes in-depth explanations of troop movements, strategy, and human stories, plus a packet of maps for further study.

This tour is particularly suited for history enthusiasts who want a tailored, informative experience. It offers a deep dive into Maryland’s Civil War significance, with an expert guide making the past tangible.

Bottom Line: If you love history and want a personal, expert-led look at Maryland’s Civil War sites, this private tour delivers depth and context.

11. Antietam National Battlefield Self-Guided Driving Tour

Number 11 provides an audio-guided driving tour for $14.99, covering the most important spots at Antietam. It’s a flexible way to explore the bloodiest single-day battle in American history at your own pace. The tour includes stops like Hawkins’ Zouaves, Mansfield Monument, and the crossfire farms, with commentary that makes each location come alive.

Many reviews emphasize how well the narration adjusts to their location, helping to visualize the battle. It’s suitable for those who prefer to self-guide but still want expert insights.

Bottom Line: For a comprehensive, flexible history experience, this self-guided tour makes visiting Antietam accessible and educational.

12. Enchanted Full Day Napa & Sonoma Wine Tour from Oakland

Number 12 takes you out West, but it’s worth mentioning for its excellent reviews. For $285, spend 8-9 hours exploring California’s famous wine regions. You visit iconic spots like Castello di Amorosa and Mayo Family Winery, tasting some of the oldest and most distinctive wines.

The tour includes views of the Golden Gate Bridge and free time at Sonoma Square, offering a taste of both wine country and scenic cityscapes.

It’s a full-day trip suited for wine lovers eager to sample different terroirs, with knowledgeable guides and access to historic wineries.

Bottom Line: While outside Maryland, this tour is ideal for travelers looking to combine scenic drives with wine tasting, especially those planning a longer trip.

13. Self-guided Waterfall Hiking Tour through Great Falls National Park

Number 13 blends outdoor adventure with ease of planning. For only $5 per person, this self-guided audio tour begins at the visitor center and guides you through the second-largest waterfall in the U.S.. It highlights hidden waterfalls, rock climbing spots, and colonial ruins, with GPS-based narration helping you find secret spots off the beaten path.

The reviews highlight how informative and fun the experience is, with plenty of opportunities for photos and exploration.

Ideal for independent travelers eager for a flexible, educational hike, this tour makes the most of Great Falls Park’s rugged beauty.

Bottom Line: For a budget-friendly, self-directed outdoor adventure, this tour is a convenient way to make the most of Great Falls’ scenic waterfalls and history.

14. Murder Mystery Detective Experience in Towson MD

Number 14 offers a quirky twist on sightseeing: a murder mystery in Towson. For $14.99 per person, you become a detective solving a staged crime across 10 locations in 2.5 hours. Using an app, you follow clues and listen to audio stories, choosing between walking or driving routes. It’s a fun, interactive way to explore the area’s streets and uncover stories in a new way.

This experience appeals to those who enjoy puzzles, storytelling, and a bit of theatricality—perfect for small groups or families wanting something different.

Bottom Line: A lighthearted, interactive mystery adventure that turns Maryland’s towns into a live game.

15. OC Bay Hopper Sunset Cruise

Finally, number 15 offers a relaxing way to end your day. The Sunset Cruise costs $35 per person and lasts about 1.5 hours. As the sun dips below the horizon, you’ll enjoy the tranquil waters of Assawoman Bay, wildlife sightings, and the changing colors of the sky.

Many reviews mention how peaceful and beautiful the trip is, with some noting the calm atmosphere perfect for unwinding after a day of exploring.

Ideal for a romantic outing or a quiet moment with friends, this cruise showcases Maryland’s evening beauty from the water.

Bottom Line: If a peaceful, scenic end to your day suits your style, this sunset cruise offers gentle relaxation and lovely views.

How to Choose Your Perfect Maryland Tour

When selecting among these diverse options, start with your interests and your schedule. For active fun and friendly competition, axe-throwing or kayaking are excellent. If you’re into history, the private Civil War battlefield tour or Antietam driving guide will deepen your understanding of Maryland’s past.

For a relaxed day, consider a scenic boat cruise like the Harborside Orange Crush or Sunset Cruise. And if you love food and culture, the Berlin Tasting Tour provides a tasty, story-rich walk.

Budget-conscious travelers might prefer the self-guided tours or bike rentals, while those seeking a guided, in-depth experience should consider the private battlefield or full-day wine tours. Booking early is wise—these popular activities fill up quickly, especially in peak seasons.

Final thoughts

Maryland’s variety of tours offers something for every traveler. Family groups might enjoy the wildlife boat trips and outdoor adventures, while history buffs will appreciate the battlefield tours and self-guided explorations.

For a laid-back experience, sunset cruises or wine tastings provide a perfect way to unwind and absorb the local scenery. With so many options, you’re sure to find a memorable way to experience Maryland’s charm.

No matter what you choose, plan ahead and book early—these experiences tend to fill up, especially during the warmer months. Maryland’s scenic beauty, history, and friendly vibe await—happy exploring!