Maryland is a state full of surprises, with a surprising variety of tours designed to fit many interests. Whether you’re into wildlife, history, outdoor activities, or good food, Maryland offers memorable ways to explore beyond the typical sightseeing. We’re particularly fond of the Assateague Island Cruise because it combines wildlife viewing with a scenic boat ride—perfect for nature lovers. The Civil War battlefield tours are a favorite for history buffs eager to walk in the footsteps of soldiers. And if you’re looking for something a little more active, renting a bike or paddling around Assateague provides a hands-on experience that’s both fun and educational. Each tour offers a different way to experience Maryland’s unique landscape and culture.
Quick Overview
Our list covers a range of adventure-filled activities, educational tours, and relaxing cruises. You’ll find options such as axe-throwing for a fun, competitive night out, scenic wildlife cruises to see the famous Assateague ponies, and culturally enriching tasting tours. For outdoor enthusiasts, kayaking and horseback riding provide immersive ways to enjoy Maryland’s natural beauty. And for history lovers, self-guided battlefield and historic town tours add depth to your visit.
1. Axe-Throwing
At number 1 on our list, the Axe-Throwing experience offers a fun twist on the usual night out. Held at a lounge in Columbia, Maryland, this activity accommodates small groups, with a maximum of 15 participants, making it perfect for friends or a small team. You’ll learn to throw axes safely, competing to see who hits the bullseye. The activity lasts about 2 hours and includes the chance to pour your own beer or wine at self-service pumps—adding a playful drinking component to the fun. The reviews highlight a perfect 5-star rating, emphasizing how enjoyable and engaging this activity is. It’s a great option if you’re looking for a lively, hands-on experience that blends skill, competition, and socializing.
Bottom Line: Ideal for groups seeking a lively, interactive outing. It’s affordable, social, and perfect for trying something completely different in Maryland.
2. Assateague Island Cruise Departs from Ocean Pines
Number 2 is the Assateague Island Cruise, a 2-hour journey that takes you to see the island’s famous wild ponies. Departing from Ocean Pines, this cruise is rated a perfect 5 stars from 22 reviews. Captain Frank and Captain Bryce are praised for their knowledgeable, friendly guidance, making the trip both fun and informative. The boat travels down Assawoman Bay, navigating around the island’s back side for a close-up view of the ponies and local wildlife, including dolphins if you’re lucky. It’s a relaxing way to experience Maryland’s coastal beauty without getting wet or sandy. This tour suits nature lovers and families who want a peaceful, scenic outing with plenty of wildlife sightings.
Bottom Line: A beautifully relaxed way to see Assateague’s ponies up close, with expert guides making the experience special.
3. Bicycle Rental from Visitor Center at Assateague
Coming in at number 3 is the Bicycle Rental at Assateague Island. For just $12, you get a bike and easy access to 6 miles of protected bike paths. This is one of the best ways to explore the island at your own pace. Reviews praise the friendly rental staff and the convenience of the location, which is right at the visitor center. Riding a bike allows you to see wild horses grazing on the beach and observe marsh overlooks and birdlife — perfect for those who enjoy outdoor activity and wildlife spotting. Plus, there’s no entrance fee when cycling into the national park, making it a budget-friendly choice for families and solo travelers alike.
Bottom Line: A simple, cost-effective way to wander Assateague and experience its natural sights at your own speed.
4. Guided Assateague Kayaking and Wildlife Discovery Tour
Number 4 is the Guided Kayaking Tour, a hands-on way to see Assateague’s ecosystems. For around $75, you’ll explore salt marshes and look for wildlife including wild horses, birds, and marine life, all with expert guides. The trip lasts about 2.5 hours and offers an intimate look at this rich habitat. Reviews point out how knowledgeable the guides are and how much fun it is to see ponies and crabs up close. Whether you’re paddling tandem or solo, this tour provides a meaningful connection with the environment, especially suited for those who want a more active experience. It’s an excellent choice for adventurers wanting to combine outdoor activity with wildlife observation.
Bottom Line: A memorable, eco-focused outing that makes you feel like you’re discovering a secret corner of Maryland’s coast.
5. Berlin Tasting Tour: A Delicious Walk Through History
Number 5 is the Berlin Tasting Tour, rated perfect 5 stars by eight reviews. This 3-hour walk explores the charming town of Berlin, Maryland, known for its small-town charm and culinary scene. You’ll visit several local restaurants and specialty shops to sample regional treats. As you stroll, learn about the families that shaped the town and discover why the Smithsonian named Berlin one of the 20 best small towns in the country. Highlights include filming locations from Runaway Bride and stories about renowned horses trained here. It’s perfect for foodies and history enthusiasts who want to combine a leisurely walk with tastings and local lore.
Bottom Line: A tasty, educational stroll that shows why Berlin is considered one of America’s coolest small towns.
6. Single Sit-On-Top Kayak Rental at Assateague Island, MD
Number 6 is a straightforward Kayak Rental, priced at $38 per person. It’s ideal for paddlers who want to explore alone at their own pace. The serene bayside setting offers chances to see ospreys, herons, and possibly even more wild ponies grazing nearby. Reviews mention how easy it is to launch from this location, and many appreciate the quiet, scenic waterways. This rental suits experienced paddlers or those willing to learn how to navigate a kayak. It’s a flexible way to spend a couple of hours soaking in Maryland’s coastal beauty independently.
Bottom Line: Perfect for confident paddlers seeking solitude and close wildlife encounters on Assateague’s waters.
7. Harborside Orange Crush Cruise
Number 7 brings you the Harborside Orange Crush Cruise, a 2-hour trip rated 5 stars. Board the OC Bay Hopper with a free orange crush cocktail, included with lunch from Harborside Bar. This lively cruise provides prime views of Assateague Island’s wild ponies, dolphins, and the waterfront. The captain shares interesting stories about the area, making it both fun and informative. It appeals to those who want a relaxed, social outing with drinks, good food, and wildlife sightings all in one. The reviews note how friendly and knowledgeable the crew are, making the experience especially enjoyable.
Bottom Line: A relaxed, social cruise combining wildlife, scenery, and a signature Maryland drink.
8. Horseback Riding Through Scenic Park in Brookeville
Number 8 is the Horseback Riding Tour, suitable for up to two people for $300. The trail winds through lush landscapes, offering a peaceful ride through Maryland’s countryside. Participants praise the private nature of the experience and the well-trained horses. If you love animals and outdoor activity, this 1.5-hour ride is a perfect way to enjoy Maryland’s scenic beauty from a new perspective. The ride is suitable for beginners and experienced riders alike, with personalized guidance ensuring a safe journey. It’s ideal for a romantic outing or a solo adventure.
Bottom Line: An intimate, scenic horseback ride for those wanting a quiet connection with nature.
9. Self-Guided Scavenger Hunt: The Fine (Art) Life in Bethesda
Number 9 offers an interactive Self-Guided Scavenger Hunt in Bethesda. For around $12, you download an app and explore at your own pace, solving challenges and trivia. It’s perfect for small groups or families wanting a flexible adventure that combines sightseeing with fun tasks. The app provides digital photos and personalized roles, making it engaging and educational. It works well for those who enjoy self-directed discovery and want to dig into Bethesda’s local art and culture in a playful way.
Bottom Line: A flexible, tech-savvy way to explore Bethesda’s streets and arts scene.
$12.31 per person
10. South Mountain Private Battlefield Tour
Number 10 is a Private Battlefield Tour led by Civil War expert Dr. Brad Gottfried. For $120 per group, you visit key sites like Gathland State Park and walk in the footsteps of soldiers who fought at South Mountain. With personalized attention and detailed maps, this 3-hour tour offers a deep dive into troop movements, human stories, and strategic significance. It’s ideal for Civil War enthusiasts who want expert insights and a tailored experience. The reviews emphasize the quality of the guide and the rich storytelling, making history come alive.
Bottom Line: A focused, educational battlefield tour for history lovers wanting expert-led insights.
$120.00 per group (up to 5)
11. Antietam National Battlefield Self-Guided Driving Tour
Number 11 is a Self-Guided Driving Tour of Antietam, rated 4 stars from 27 reviews. For just $14.99, you get an audio guide to explore the battlefield at your own pace. It highlights key spots like the Mansfield Monument and major crossing points, giving a detailed narrative of this pivotal Civil War battle. The flexibility of a self-guided tour makes it perfect for those with limited time or who prefer to explore independently. Reviewers appreciate how well the narration brings history to life and helps visualize the battle.
Bottom Line: An affordable, flexible way to learn about Antietam without a guide, suited for history buffs and repeat visitors.
12. Enchanted Full Day Napa & Sonoma Wine Tour from Oakland
Number 12 takes you on a Full-Day Wine Tour, rated 4.5 stars. Starting from Oakland, you visit famous wineries like Castello di Amorosa, Mayo Family Winery, and Sonoma Square. The 8-9 hour trip includes scenic drives, wine tastings, and some free time to explore. For around $285, this tour offers great value with insider visits to historic wineries known for their craftsmanship. It’s perfect for wine lovers who want a taste of California’s renowned vineyards, while still enjoying the scenic route through the Bay Area.
Bottom Line: A comprehensive, full-day experience for wine enthusiasts seeking quality tastings and scenic views.
13. Self-guided Waterfall Hiking Tour through Great Falls National Park
Number 13 is a Self-Guided Waterfall Hike for just $5. It uses an app with GPS and narration to lead you through Great Falls Park, highlighting waterfalls, hidden spots, and even colonial-era ruins. The 2-3 hour hike is suitable for independent travelers and adventure-seekers wanting to explore on their own terms. Reviews mention how well the app’s commentary enhances the visit and helps find lesser-known features like rock climbing spots. It’s ideal for those comfortable with navigation and wanting a more active, personalized experience.
Bottom Line: A budget-friendly, self-paced hike that reveals Maryland’s natural and historical highlights.
14. Murder Mystery Detective Experience in Towson MD
Rated 4.5 stars, this Murder Mystery puts you into the shoes of a detective solving a crime around Towson. For $14.99, the 2.5-hour experience includes exploring 10 locations via walking or driving maps, and listening to a gripping audio story. It’s perfect for small groups or solo travelers who like interactive storytelling and puzzle-solving. Reviewers praise how well-designed the app and mystery are, making it a fun, lighthearted way to explore Towson’s streets.
Bottom Line: A fun, interactive urban adventure for puzzle enthusiasts and mystery fans.
15. OC Bay Hopper Sunset Cruise (Departs From Ocean Pines)
Number 15 offers the Sunset Cruise, a peaceful 1.5-hour trip rated 4 stars. As the sun dips, you can unwind with a beverage, enjoy the calm waters, and spot wildlife like dolphins and marsh birds. It’s a perfect way to end a day of exploring, especially if you enjoy a relaxed atmosphere and scenic views. The cruise is very intimate, often with small groups, making it feel like a private outing. It’s suitable for couples or anyone wanting a quiet, scenic experience at the close of the day.
Bottom Line: A peaceful, scenic way to enjoy Maryland’s waterways at sunset.
16. Chesapeake Beach: Guided Walking Tour of the Railway Trail
Finally, the Railway Trail Tour in Chesapeake Beach offers a 1.5-hour walk focusing on local history and nature. You’ll learn how the trail helped establish the town and see wildlife like bald eagles and purple martins. The route includes educational gardens for learning about native plants and how to repel mosquitos naturally. While reviews are not available, this tour suits outdoor lovers interested in history and ecology alike, with a relaxed pace and scenic views.
Bottom Line: A short, educational walk that blends history, wildlife, and nature.
$41 per person
How to Choose Your Maryland Tour
When selecting a tour, consider your budget, interest, fitness level, and available time. If you want a fun, social night, axe-throwing is a great pick. For wildlife and scenic waterways, the Assateague cruises or kayaking are excellent options. History enthusiasts may prefer the Civil War battlefield tours or Antietam self-guided driving. Food lovers should check out the Berlin Tasting Tour, which combines culinary delights with local stories. And for active explorers, renting bikes or kayaks offers an immersive experience.
Booking early is recommended, especially for popular outdoor activities in peak season, and always check the weather forecast to ensure the best experience.
Final Thoughts
Maryland’s diversity in tours ensures there’s something for every type of traveler. For a lively night out, axe-throwing is a fun choice. Wildlife lovers will enjoy the boat trips and kayaking adventures, while history buffs can enjoy battlefield tours and historic towns. Food and wine enthusiasts have options like the Berlin Tasting Tour and Napa Valley trips, making Maryland more than just a place to pass through.
No matter your interests, these tours provide authentic ways to see Maryland’s natural beauty, rich history, and local flavor. Consider your priorities, plan ahead, and don’t forget to book early—many of these experiences fill up quickly, especially in good weather. Now, all that’s left is to pick your perfect tour and enjoy everything Maryland has to offer.