Making the Most of Maryland: Group-Friendly Destinations
Maryland may be small, but it’s packed with group-friendly destinations perfect for day trips, weekend getaways, and special celebrations. While popular places like Baltimore and Ocean City tend to dominate travel guides, there’s something to be said for the hidden gems—the spots locals love that haven’t been overrun by tourists. Whether you’re planning a family reunion, a getaway with friends, or a school or community outing, there are plenty of places across the state where group travel really shines.
This guide rounds up some of Maryland’s lesser-known but unforgettable destinations—plus a few honorable mentions just outside our borders. If you’re looking for variety, charm, and scenery, you’ve come to the right place.
Chesapeake City
Chesapeake City is a tiny waterfront town along the Chesapeake & Delaware Canal that feels like a step back in time. With 19th-century buildings, boutique shops, cafés, and waterfront dining, it’s a charming destination for a relaxed group outing. The walkable downtown makes it easy to explore together, and the scenic views are hard to beat. Whether you’re planning a ladies’ lunch, a photography club outing, or a multigenerational family trip, Chesapeake City offers quiet charm and a refreshing change of pace.
Deep Creek Lake
Tucked away in Western Maryland, Deep Creek Lake is a year-round destination with plenty for groups to do. Summertime means pontoon boats, paddleboards, and scenic hikes around Swallow Falls State Park. Rentals in the area are often designed for families or larger groups, making it an easy getaway with charter travel. Whether you’re into water activities, mountain views, or cozying up around a fire pit, it’s an ideal escape.
St. Michaels
St. Michaels blends maritime history with small-town charm. It’s great for group outings, such as family reunions, bridal showers, or corporate retreats, thanks to its walkable waterfront, boutique lodging, and numerous activities to enjoy. The Chesapeake Bay Maritime Museum is a must-see, and the ferry from Annapolis adds a scenic start to your trip. With plenty of outdoor space and historic sites, it balances relaxation and exploration perfectly.
Patapsco Valley State Park
Located just west of Baltimore, Patapsco Valley State Park is a nature lover’s dream, offering hiking, biking, picnic shelters, and even a suspension bridge. Spanning over 16,000 acres, it’s big enough to spread out but close enough for an easy day trip. Charter transportation makes it simple to coordinate drop-offs and pickups at different entry points, especially for youth groups or multi-family gatherings.
Catoctin Mountain Park & Cunningham Falls State Park
These sister parks, located near Maryland’s northern border, offer stunning views and outdoor fun. Catoctin Mountain is renowned for its scenic overlooks and historic sites, including Catoctin Furnace. Cunningham Falls is home to the state’s largest waterfall—a group photo favorite. Together, they make a great low-cost option for hiking and picnicking. With clear trails, picnic areas, and historic charm, they’re ideal for groups looking for a breath of fresh mountain air.
Havre de Grace
Located where the Susquehanna River meets the Chesapeake Bay, Havre de Grace is known for its waterfront boardwalk, the Concord Point Lighthouse, and small-town charm. It’s a peaceful spot for antiquing, wine tasting, or just enjoying the views. With its scenic beauty and historic touches, it’s a favorite for day trips and slow-paced group outings.
Solomons Island
Solomons Island sits at the mouth of the Patuxent River in Southern Maryland and offers plenty of arts, culture, and waterfront fun. From the Annmarie Sculpture Garden to the Calvert Marine Museum, there’s no shortage of things to do. It’s a laid-back spot with great dining and even better sunsets—one of Southern Maryland’s true group-friendly destinations, perfect for milestone birthdays or small retreats.
Frederick
Frederick combines historic flair with modern fun. It’s walkable, filled with local shops and breweries, and home to sites like the Monocacy National Battlefield. Private tastings and patio hangouts make it a great choice for adults looking to unwind, while the town’s history offers something for everyone. Think girls’ weekends, multi-family adventures, or even arts-focused field trips.
Honorable Mentions: Just Beyond Maryland
While Maryland has plenty to offer, don’t rule out nearby destinations that are easily accessible for group travel. Sometimes crossing state lines just a little opens up big opportunities for new experiences, without the stress of long-distance planning.
- Harpers Ferry, WV – Perfect for hiking, guided tours, and a blend of nature and history
- Old Town Alexandria, VA – A charming riverside town with colonial appeal and boutique shopping
- Rehoboth Beach, DE – A quieter, family-friendly alternative to Ocean City with a classic boardwalk vibe
- Gettysburg, PA – Rich in Civil War history, perfect for educational group trips or history buffs
These locations are close enough to make sense for a weekend trip, and chartering transportation helps make the journey just as enjoyable as the destination.
Group-Travel Made Easy with Chesapeake Charter
Whether you’re planning a day trip to a scenic park or a weekend getaway with the whole crew, charter transportation takes the pressure off. No carpool coordination, no parking headaches—just one smooth, comfortable ride. Plus, our professional drivers and modern fleet help ensure a safe and relaxed experience from start to finish.
Let Chesapeake Charter help you explore more of what Maryland—and beyond—has to offer. Our experienced team and versatile fleet make group travel easier, so you can focus on the fun.
Ready to start planning your group adventure? Contact us today to request a quote, and let’s get rolling.
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