TOP 30 Best Outdoor adventures in Annapolis, Maryland

Annapolis Sailing Adventures is a premier travel agency located in Annapolis, Maryland, United States. We offer a variety of sailing experiences, including private charters, sunset cruises, and sailing lessons. Our experienced captains will take you on a memorable journey on the beautiful Chesapeake Bay. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Annapolis Sailing Adventures has something for everyone. Come aboard and experience the thrill of sailing in one of the most scenic locations in the United States.

Waypoints Annapolis is a premier travel agency located in the heart of Annapolis, Maryland. Situated at 222 Severn Avenue, our agency specializes in creating unforgettable travel experiences for our clients. Whether you're looking to plan a romantic getaway, a family vacation, or a business trip, our team of experienced travel experts is here to help. From booking flights and accommodations to arranging tours and activities, we take care of all the details so you can relax and enjoy your journey. Trust Waypoints Annapolis to guide you to your next adventure.

Pirate Adventures on the Chesapeake, located at 311 Third Street in Annapolis, Maryland, is a top tourist attraction and travel agency offering a unique and exciting experience for families. Guests rave about the high-energy and memorable adventures provided by the enthusiastic pirate crew. From searching for sunken treasure to firing water cannons, kids of all ages are sure to have a blast on this pirate cruise. The institution is highly recommended for parents of young children, as well as for school field trips. With activities like pirate dress up, face-painting, and interactive storytelling, Pirate Adventures on the Chesapeake is a must-visit destination for families looking for outdoor fun and entertainment. Don't miss out on this unforgettable experience – book your reservation today and set sail for a day filled with laughter and exploration!

Annapolis Rock Vista is a breathtaking tourist attraction located in Boonsboro, Maryland, United States. This stunning vista offers panoramic views of the surrounding landscapes, making it a popular destination for nature lovers and outdoor enthusiasts. Visitors can hike to the rock formation to enjoy the scenic overlook, perfect for photography or simply soaking in the natural beauty. Annapolis Rock Vista is a must-visit destination for anyone looking to experience the beauty of Maryland's wilderness.

Annapolis Rock & Black Rock Cliff Trailhead is a park and tourist attraction located at 11175 Baltimore National Pike in Myersville, Maryland, United States. It is part of South Mountain State Park, managed by the Maryland Department of Natural Resources. The park offers a 40-mile long multi-use trail weaving along the South Mountain ridge, offering visitors a variety of geologic, natural, cultural, and historic experiences. Visitors can walk in the footsteps of Civil War soldiers, climb to breathtaking views, and experience the solitude of nature. The park is home to the Appalachian National Scenic Trail, with scenic overlooks at Weverton Cliffs, Annapolis Rocks, and High Rock providing amazing views of the landscape. Designated camping areas and shelters are available for backpackers and thru-hikers on a first-come-first served basis.

Annapolis Canoe and Kayak is a premier store located in the heart of Annapolis, Maryland. We offer a wide selection of canoes and kayaks for all levels of paddlers, from beginners to experienced enthusiasts. Our knowledgeable staff is dedicated to helping you find the perfect watercraft for your needs, whether you're looking for a leisurely paddle on the bay or a thrilling whitewater adventure. Visit us at 311 Third Street to browse our inventory and get expert advice on all things paddling.

Navy Getaways Annapolis Suites, RV Park, Campground, and Cottages is a new institution set to open in 2022 at 2 Truxtun Road in Annapolis, Maryland, United States. This facility will offer a range of accommodations including suites, RV sites, and cottages for visitors looking to enjoy a peaceful and scenic getaway. The campground and park will provide a tranquil setting for guests to relax and unwind, with various outdoor activities and amenities available. Stay tuned for the grand opening of Navy Getaways Annapolis in 2022!

Visit Annapolis & Anne Arundel County is a premier tourist attraction and travel agency located at 26 West Street in Annapolis, Maryland, United States. This institution offers a wide range of services to help visitors explore and experience the beauty and charm of Annapolis and Anne Arundel County. From guided tours of historic sites and museums to booking accommodations and dining reservations, Visit Annapolis & Anne Arundel County is your one-stop destination for all things travel-related in this picturesque region. Whether you're a history buff, outdoor enthusiast, or foodie, this institution has something for everyone to enjoy during their visit to Annapolis and Anne Arundel County.

The Baltimore-Annapolis Trail Park is a picturesque outdoor destination located in Severna Park, Maryland. This beautiful park offers a scenic trail for hiking, biking, and leisurely walks, surrounded by lush greenery and stunning views. Visitors can enjoy a peaceful escape from the city and immerse themselves in nature at this popular tourist attraction. With its convenient location and well-maintained facilities, the Baltimore-Annapolis Trail Park is the perfect place to spend a day outdoors with family and friends.

Helly Hansen Annapolis is a premier clothing store located at 132 Main Street in the charming city of Annapolis, Maryland. Specializing in high-quality outdoor apparel and gear, this store offers a wide selection of jackets, pants, shirts, and accessories for all your outdoor adventures. Whether you're sailing on the Chesapeake Bay or exploring the historic streets of Annapolis, Helly Hansen has you covered with durable and stylish clothing that will keep you comfortable in any weather conditions. Visit Helly Hansen Annapolis for all your outdoor clothing needs and gear up for your next adventure!

The North Face Westfield Annapolis is a premier outdoor retail store located in Annapolis, Maryland. With a wide selection of clothing, shoes, and gear for all your outdoor adventures, this store is a must-visit for outdoor enthusiasts. Whether you're looking for hiking boots, winter jackets, or backpacks, you'll find everything you need at The North Face. Visit us at 2002 Annapolis Mall Road and gear up for your next outdoor excursion.

Musto Annapolis is a premier clothing store located in the heart of Annapolis, Maryland. Situated at 118 Main Street, this store offers a wide selection of high-quality Musto apparel and gear for sailors, outdoor enthusiasts, and anyone looking for stylish and functional clothing. From technical sailing gear to casual wear, Musto Annapolis has something for everyone. Visit us today to explore our collection and find the perfect outfit for your next adventure.

The Annapolis Waterworks Trail - Housley Rd Trailhead is a beautiful park located at 2607 Housley Road in Annapolis, Maryland, United States. This scenic trailhead offers visitors the opportunity to explore the surrounding natural beauty and enjoy a peaceful outdoor experience. Whether you're looking for a leisurely walk, a challenging hike, or a place to simply relax and unwind, this park has something for everyone. With well-maintained trails, lush greenery, and scenic views, the Annapolis Waterworks Trail - Housley Rd Trailhead is the perfect destination for nature lovers and outdoor enthusiasts alike.

Capital SUP at Quiet Waters Park in Annapolis, Maryland offers a variety of stand-up paddle board and kayak experiences for all ages. Join our award-winning Summer Camp for kids, featuring four days of adventure and education on the water. Learn how to paddle, participate in fun races and games, and explore the waterways of Annapolis. Monthly and seasonal membership options are available for unlimited paddling opportunities. Rent a stand-up paddleboard or kayak to explore Harness Creek off the South River, or check out our new location at Nautilus Point Marina on Back Creek. Our team of experienced staff members are available to assist you in and out of the water, ensuring a safe and enjoyable experience.

Capital SUP - Eastport is a health institution located at 655 Americana Drive in Annapolis, Maryland, United States. Offering Annapolis Stand Up Paddle Board & Kayak Experiences, this award-winning institution provides a variety of activities for all ages. From paddleboarding to kayak rentals, there is something for everyone to enjoy on the beautiful waterways of Annapolis. For those looking for a fun and educational experience, Capital SUP offers a four-day summer camp at Quiet Waters Park. Kids can learn how to paddle, participate in races, fitness classes, games, and even oyster education. Monthly and seasonal membership options are also available for unlimited paddling opportunities.

East of Maui is a premier store located in Annapolis, Maryland, United States, offering a wide range of water sports equipment and gear. Situated at 2444 Solomons Island Road, this institution is a one-stop shop for all your surfing, paddleboarding, and kayaking needs. With a knowledgeable staff and top-quality products, East of Maui is the perfect destination for outdoor enthusiasts looking to explore the waters of Maryland. Whether you're a beginner or an experienced water sports enthusiast, you'll find everything you need at East of Maui to make the most of your time on the water.

Quiet Waters Park is a serene oasis nestled in the heart of Annapolis, Maryland. This picturesque park covers over 340 acres and offers a peaceful escape from the hustle and bustle of city life. Visitors can enjoy a variety of outdoor activities such as hiking, picnicking, and biking along the scenic trails. The park also features a beautiful lake where guests can go fishing or paddle boating. With its lush greenery, tranquil atmosphere, and stunning views, Quiet Waters Park is a popular tourist attraction for nature lovers and outdoor enthusiasts alike.

Anglers Sport Center is a one-stop shop for all your outdoor and fishing needs in Annapolis, Maryland. Located at 1456 Whitehall Road, this institution offers a variety of clothing, food, and liquor options for outdoor enthusiasts. Whether you are a seasoned angler or hunter, or just starting out, Anglers has everything you need to make your outdoor adventures a success. With a knowledgeable staff and excellent customer service, Anglers Sport Center is the go-to destination for all things hunting and fishing in Annapolis. Visit us today and gear up for your next outdoor excursion!

Ski Haus Sports Center is a premier sports retail destination located at 824 East College Parkway in Annapolis, Maryland. As a one-stop shop for all your outdoor needs, Ski Haus offers a wide selection of bicycles, clothing, and gear for outdoor enthusiasts of all levels. Whether you're hitting the trails on two wheels or gearing up for a day on the slopes, Ski Haus has everything you need to stay active and stylish. Visit us today and let our friendly and knowledgeable staff help you find the perfect gear for your next adventure.

Come enjoy the beauty of Bladensburg Waterfront Park, located along the historic Anacostia River in Maryland, United States. Whether you prefer to explore the river by boat or hike/bike on the trails, there is something for everyone to enjoy. The park offers a variety of engaging programs for all ages, including boat tours, hikes, bike rides, and paddle events. Advance registration is required for most programs, so be sure to secure your spot in advance. Additionally, the park offers educational science and social studies programs for students from Preschool to 12th grade, both on-site and at schools/facilities. Come aboard the pontoon boat for an interpretive riverboat tour and explore the scenic Anacostia River. Life jackets are provided for your safety. Don't miss the opportunity to visit the newly renovated B&O Caboose, where students can learn about train history and explore different parts of the train car. Join us at Bladensburg Waterfront Park for a fun and educational outdoor experience!"

Truxtun Park is a beautiful and expansive park located at 273 Hilltop Lane in Annapolis, Maryland. This popular tourist attraction offers a variety of recreational activities for visitors to enjoy, including walking trails, playgrounds, sports fields, and picnic areas. The park also features a serene pond, perfect for fishing or simply relaxing by the water. With its lush greenery and scenic views, Truxtun Park is a must-visit destination for nature lovers and outdoor enthusiasts alike.

Jonas and Anne Catharine Green Park is a picturesque and peaceful park located at 2001 Baltimore Annapolis Boulevard in Annapolis, Maryland, United States. This charming park is a popular tourist attraction, offering visitors a serene escape from the hustle and bustle of city life. With lush greenery, walking paths, and beautiful views, this park is the perfect spot for a leisurely stroll, a picnic with loved ones, or simply to relax and unwind. Whether you're a local looking for a quiet retreat or a tourist exploring the area, Jonas and Anne Catharine Green Park is a must-visit destination for nature lovers and outdoor enthusiasts alike.

Nestled along the serene banks of the Patuxent River in Maryland, Goose Creek Campground offers a picturesque setting for outdoor enthusiasts and nature lovers alike. This charming campground provides a variety of lodging options, from tent sites to RV hookups, ensuring a comfortable stay for all visitors. Surrounded by lush greenery and scenic views, guests can enjoy fishing, hiking, and other outdoor activities within the campground's expansive park grounds. Whether you're seeking a peaceful retreat or an adventurous getaway, Goose Creek Campground is the perfect destination for a memorable outdoor experience.

Bulldog Bikes and Floats is a one-stop shop for all your biking and water recreation needs. Located at 504 Baltimore Annapolis Boulevard in Severna Park, Maryland, this store offers a wide selection of bicycles, bike accessories, and water floats for all ages and skill levels. Whether you're looking for a new bike to hit the trails or a fun float to relax on the water, Bulldog Bikes and Floats has you covered. With friendly and knowledgeable staff ready to assist you, this institution is the perfect destination for outdoor enthusiasts in the Severna Park area.

Eddie Bauer is a renowned clothing store located at 1835 Annapolis Mall Road in Annapolis, Maryland, United States. Specializing in outdoor apparel, footwear, accessories, and gear, Eddie Bauer is known for its high-quality, durable products that are built to withstand the elements. With a history spanning over 100 years, Eddie Bauer has been a trusted source for adventurers looking to explore the great outdoors. Whether you're hiking, camping, or simply enjoying a stroll in nature, Eddie Bauer has the gear you need to make the most of your adventure.

EscapeTime is a mobile escape room institution located in Annapolis, Maryland. Similar to a traditional escape room, teams must work together to solve puzzles, discover clues, and escape before time runs out. Our mobile escape room is perfect for corporate team building, birthday parties, student groups, holiday celebrations, and more. The experience lasts 10 minutes and is sure to get your adrenaline pumping! Our game master will ensure a unique and memorable experience for all ages, from 5 to 100. The mobile trailer can accommodate 4-6 players at a time and can be set up in various outdoor locations. We require a standard electrical hook up or can bring a generator at no extra cost.

Classic Sail Charters is a premier sailing school located in Annapolis, Maryland, offering private sailing adventures for up to six passengers. With world-class sailing yachts, experienced captains, and top-notch service, we ensure that your charter experience is truly unforgettable. Our charters are exclusively for private parties, allowing you to customize your adventure. Join us at 980 Awald Road for a unique and luxurious sailing experience on the beautiful Siena yacht. With Captain Nate, Payton, and Tony at the helm, you can relax, learn some sailing skills, and enjoy the stunning views of the West River. Whether you're looking for a romantic engagement shoot, a family outing, or a relaxing day on the water, Classic Sail Charters has something for everyone. Book your trip today and set sail for an unforgettable experience on the Chesapeake Bay.

Deep Creek View is a premier institution located in the picturesque town of Annapolis, Maryland, United States. Situated with a stunning view of Deep Creek, our institution offers a serene and tranquil environment for learning and personal growth. Our state-of-the-art facilities and dedicated faculty provide a top-notch educational experience for students of all ages. Whether you're looking to further your academic career or simply enjoy the beauty of the surrounding nature, Deep Creek View is the perfect place for you. Come visit us and see for yourself the unique opportunities that await at Deep Creek View.

Anne Arundel County Recreation & Parks is a local government office located at 1 Harry S. Truman Parkway in Annapolis, Maryland, United States. This institution is dedicated to providing a wide range of recreational and leisure opportunities for residents and visitors of all ages. From sports leagues and fitness classes to nature programs and community events, Anne Arundel County Recreation & Parks strives to enhance the quality of life for everyone in the community. Their mission is to promote health, wellness, and social connection through accessible and affordable recreational activities. Visit their office or website to learn more about their programs and services.

Island Chill Yacht Charters (ICYC) is a travel agency located at 1444 Shore Drive in Edgewater, Maryland, United States. We specialize in creating the 'Relaxing Excitement of the Islands' on private sail and powerboat cruises for families, friends, and couples. Conveniently situated in historic Londontowne, we are close to Washington D.C. and Baltimore, just 6 miles south of Annapolis - the 'Sailing Capital of America!' Our cruises are perfect for hot summer days and chill sunsets, making them ideal for birthdays, anniversaries, bachelorette parties, corporate retreats, national holidays, and special events. Choose from our 43-foot sailboat (Therapy), 34-foot powerboat (Irie Vibes), or 20-foot bow-rider powerboat (Tallawah) for captained cruises along the South and Rhode Rivers, Chesapeake Bay, and Thomas Point Shoal Lighthouse. Enjoy swimming, paddle boarding, floating lily pads, sunbathing, beaches, sandbars, islands, kayaking, and fishing options.