Maryland’s best tours concentrate in three main categories: wine, food, and history. The standout wine tours weave through Chesapeake’s picturesque vineyards, offering intimate tastings at family-owned estates. Food walking tours in Berlin and Salisbury get straight to the point, connecting visitors with authentic Maryland cuisine and local restaurant owners. For history seekers, the North Beach Historic tour and Railway Trail in Chesapeake Beach tell compelling stories of the region’s maritime and railroad past – both well-organized and rich in detail.
I love the Berlin food tour for its perfect mix of small-town charm and surprising culinary variety, while the Chesapeake wine route impresses with its knowledgeable guides and generous pours.
Let’s look at our favorite Maryland tours, ranked by experience and value.
Key Points
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Wine, beer, and spirit tours offer an immersive experience exploring local wineries, breweries, and distilleries in destinations like Frederick and the Chesapeake region.
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Culinary and food tours provide a delectable exploration of regional flavors and local cuisine in towns like Berlin and Salisbury.
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Walking and historical tours in Chesapeake Beach explore the area’s rich heritage, natural wonders, and cultural significance.
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Educational and cultural insights are woven into tours, enabling visitors to learn about the history, wildlife, and artifacts of Maryland’s coastal regions.
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Tours in Maryland offer accessible, family-friendly experiences with convenient locations, transportation options, and flexible reservation policies for diverse traveler needs.
Wine Beer and Spirit Tour in Frederick
For visitors eager to explore Frederick’s vibrant beverage scene, the Wine Beer and Spirit Tour offers a delightful half-day journey. This small-group excursion takes travelers to three local wineries, breweries, and distilleries, allowing them to sample a selection of the region’s finest wines, beers, and spirits.
The tour includes round-trip transportation from a central meeting point, tasting fees, and a collectible wine glass or tote bag. Travelers can also opt for a cheese or charcuterie plate and enjoy lunch and snacks during the tour. The air-conditioned vehicle ensures a comfortable experience, and bottled water is provided.
With a maximum of 10 travelers per tour, the experience offers an intimate and personalized exploration of Frederick’s burgeoning beverage industry. However, a minimum group size of 8 is required, and the tour is restricted to those 21 and older with a moderate fitness level.
While past reviews have been largely positive, there have been some concerns about service reliability.
Read our full review: Wine Beer and Spirit Tour in Frederick Review
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Maryland: Chesapeake Region Wine Tour With Lunch & Tastings
Travelers can embark on a delightful wine tour through Maryland’s Chesapeake region. This guided tour takes visitors to several renowned wineries, offering a chance to sample a diverse array of locally-produced wines.
The tour includes a leisurely lunch, providing an opportunity to savor the flavors of the region while taking in the scenic beauty of the Chesapeake landscape.
Participants will visit wineries that specialize in producing a variety of wines, from crisp whites to bold reds. Expert guides will lead tastings, sharing insights into the winemaking process and the unique terroir of the Chesapeake region.
Between tastings, guests can explore the charming tasting rooms and grounds of the wineries, gaining a deeper appreciation for Maryland’s thriving wine culture.
The Maryland: Chesapeake Region Wine Tour with Lunch & Tastings is an ideal way for wine enthusiasts to discover the exceptional quality and diversity of Maryland’s local vintages while enjoying the picturesque settings of the Chesapeake countryside.
Read our full review: Maryland: Chesapeake Region Wine Tour With Lunch & Tastings Review
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Chesapeake Region Wine Tour
Explore the captivating Chesapeake wine region on this guided tour, often overlooked by visitors.
You’ll visit two local wineries, meet the winemakers, and sample a variety of reds and whites. The small-group format ensures a personalized experience as you explore the region’s vibrant wine culture.
The tour includes tasting fees, a collectible wine glass and tote bag, and an optional cheese and fruit or charcuterie platter.
Lunch, bottled water, and snacks are provided, along with transportation in an air-conditioned vehicle. Additional alcoholic drinks can be purchased.
The tour starts at 11:00 am at the Chesapeake Heritage & Visitors Center. Participants must be 21 or older and dress in smart casual attire, with comfortable shoes recommended.
The moderate physical fitness level required is suitable for most. Booking confirmation is received unless made within 2 days of travel, and a minimum of 8 passengers is needed to operate the tour.
Read our full review: Chesapeake Region Wine Tour Review
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Chesapeake Beach: North Beach Historic Guided Walking Tour
This guided walking tour of North Beach offers visitors a captivating glimpse into the town’s rich history.
Lasting 1.5 hours and priced at £35.73 per person, the tour is limited to just 6 participants, ensuring an intimate and personalized experience.
Led by a knowledgeable guide, the tour explores the town’s historic landmarks, including the colorful boardwalk, the famous fishing pier, and the Bayside History Museum.
Along the way, guests will learn about the town’s rich cultural heritage and discover hidden gems in the town center.
The tour’s flexibility allows for free cancellation up to 24 hours in advance, and guests can reserve their spot without paying upfront.
With a minimum of 5 participants required, the tour ensures a shared experience with fellow history enthusiasts.
Whether you’re a local or a visitor, the North Beach Historic Guided Walking Tour provides an engaging and educational way to explore the charming town of Chesapeake Beach.
Read our full review: Chesapeake Beach: North Beach Historic Guided Walking Tour Review
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Berlin Tasting Tour: A Delicious Walk Through History
Although located in the charming town of Berlin, Maryland, the Berlin Tasting Tour offers visitors a delightful journey through the area’s rich culinary history.
This 3-hour walking tour, priced at $110 per person, takes participants to various local eateries, where they can sample a variety of delicious regional dishes.
The tour, which accommodates a maximum of 12 travelers, is accessible to wheelchair users, stroller-pushers, and those with service animals.
Participants will meet at 119 N Main St, Berlin, MD 21811, at 11:00 am, and the tour will return to the same location.
With a perfect 5.0 rating based on 8 reviews, the Berlin Tasting Tour is a must-do activity for anyone exploring the flavors of Maryland.
Lunch is included, and the tour highlights the area’s delectable cuisine and captivating history.
Read our full review: Berlin Tasting Tour: A Delicious Walk Through History Review
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Chesapeake Beach: Guided Walking Tour of the Railway Trail
Moving from the delightful culinary exploration in Berlin, visitors can now embark on a guided walking tour that uncovers the historic Railway Trail in the charming coastal town of Chesapeake Beach, Maryland.
This 1.5-hour tour, limited to just 6 participants, allows guests to discover the trail’s significant role in establishing Chesapeake Beach. Led by a live guide, the walking tour starts and ends at Kellams Field, where explorers can observe local wildlife, including bald eagles.
Along the way, they’ll visit an educational garden to learn about repelling mosquitos with plants and how to support wildlife with bat and purple martin houses. The tour costs $41.20 per person and offers free cancellation up to 24 hours in advance.
With a reserve now, pay later option, visitors can secure their spot without immediate payment. Minimum group size is 5, ensuring an intimate and informative experience exploring this historic Maryland destination.
Read our full review: Chesapeake Beach: Guided Walking Tour of the Railway Trail Review
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Heart of Savory Salisbury Foodie Tour
Embarking on the Heart of Savory Salisbury Foodie Tour provides visitors a delectable exploration of Salisbury’s vibrant culinary scene. This 5-star rated tour takes guests on a journey through the heart of the city, with a maximum of 12 travelers per group.
The tour departs from the Market Street Inn, where you will be picked up near the bar, identifiable by the lollipop sign with the OC Foodie Tour logo.
The 2-hour tour includes a complimentary lunch and private transportation, ensuring a comfortable and convenient experience. Accessibility is a priority, with the tour being wheelchair and stroller accessible, and service animals welcome.
Whether you’re a local or a visitor, this tour offers a unique opportunity to discover the flavors that define the heart of Salisbury. With its rave reviews and convenient meeting location, the Heart of Savory Salisbury Foodie Tour is a must-try for any food enthusiast exploring Maryland.
Read our full review: Heart of Savory Salisbury Foodie Tour Review
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Chesapeake Beach: North Beach Scenic Guided Walking Tour
The North Beach Scenic Guided Walking Tour in Chesapeake Beach offers visitors a captivating exploration of the area’s natural beauty and rich history. Priced at €39.39 per person, the 1.5-hour tour is limited to just 6 participants, ensuring a more personalized experience.
The tour begins at the Welcome Center on the Board Walk, where a live guide provides insights and historical context.
Highlights include admiring the Sunrise Garden’s water features, native plants, and sculptures, and spotting migratory birds and local wildlife at the Wetland Overlook Park. Guests will also discover the fishing pier and learn about famous entertainers discovered there.
The tour culminates at the Bayside History Museum, where visitors can view exhibits showcasing shark teeth, whale bones, Native American implements, sea shells, and coral.
With a flexible reservation and free cancellation policy, the North Beach Scenic Guided Walking Tour is an excellent way to take in the natural and cultural wonders of Chesapeake Beach.
Read our full review: Chesapeake Beach: North Beach Scenic Guided Walking Tour Review
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Sum Up
Maryland offers a variety of engaging tours that allow visitors to explore the state’s rich history, thriving food and beverage scene, and stunning natural landscapes. From wine and spirit tastings to walking tours of historic towns and trails, these tours provide an immersive experience that showcases the best of what Maryland has to offer. Whether you’re a local or a tourist, there’s a tour that will suit your interests and enhance your appreciation for the state’s diverse attractions.