Weekend Getaway

Cruising the Massachusetts Coast - Boston

New England
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By
Anna
Barthelme
Boston, Massachusetts

Exploring history-rich Boston, on Massachusetts coast, is one of the best summer cruising adventures on the East Coast. The area has been home to a wealth of significant events throughout the centuries, from the Boston Massacre to the Boston Tea Party to the Battle of Bunker Hill. It's a one-of-a-kind destination that makes for an exciting weekend you won't forget.

Tie up your dinghy along the Charles River at Community Boating Inc., and enjoy a delightful day wandering down Newbury Street. The charming eight-block area is filled with salons, boutiques, and spectacular dining choices. Swing by the Flour Bakery (617-437-7700) for the excellent pastries, sandwiches and salads.If you fancy exercise, you can run, skate, or ride bikes along the historic 18-mile-long Charles River Esplanade, which runs parallel to the entire basin on both the north and south sides of the Charles River waterfront. If you're a baseball fan, don't miss a tour of or better yet, a game at Fenway Park (617-226-6666, boston.redsox.mlb.com), the oldest major league park in the U. S. and home to the Boston Red Sox. When it's time for dinner, you'll be spoiled for choices, as Boston is full of top- notch restaurants. One perennial favorite is the Top of the Hub Restaurant & Lounge (617-536-1775), which features contemporary New England dishes and stunning views of downtown. If you're near the area on the Fourth of July, relax along the banks of the Charles and catch the annual Boston Pops Fireworks Spectacular (july4th.org).

Great dockage can be found in the city's famed North End neighborhood at Boston Yacht Haven (617-367-5050, thebostonyachthaven.com), or at Constitution Marina (617-241-9640, constitutionmarina.com), which is set along the historic Freedom Trail.

For a quick trip through the city by water, travel down the Charles River through the locks to Cambridge, home to Harvard and MIT, and visit the Galleria Mall, Central Square, and Harvard Square.

Day 1: Plymouth, Massachusetts

Located just 35 miles south of Boston, the quaint town of Plymouth was one of the first colonies founded by the pilgrims in 1620. The town is best known as the setting of the original Thanksgiving feast and is filled with historic buildings, museums, and monuments, including the 1749 Court House and Museum, the First Church, Burial Hill, and the Mayflower II (a replica of the original Mayflower).

Stroll along the cobblestone walkways of the Village Landing Marketplace, a shopping district of boutiques, specialty shops, restaurants and cafes. Hungry? Hit the Plymouth Harbor waterfront and stop at the East Bay Grille (508-746-9751), to enjoy live entertainment Wednesday through Saturday. Another fun experience is joining a ghost and legends walk with Colonial Lantern Tours (774-454-8126). Dock at Brewer Plymouth Marine (508-746-4500, byy.com/Plymouth) a full-service marina within walking distance of town.

Day 2: Gloucester, Massachusetts

About 45 miles north of Plymouth is Gloucester, the center of New England's fishing industry. The city is home to the oldest seaport in the country. Ever seen the popular National Geographic show Wicked Tuna? That's exactly what this town is all about: bluefin tuna.

Soak up the rays at Good Harbor Beach or Wingaersheek Beach, both of which are kid friendly. Bring your appetite to take advantage of one of the state's best seafood restaurants: the Gloucester House (888-283-1812). Prefer to dock and dine? Head to Rudder Restaurant (978-283-7967), known for its wicked-cool atmosphere and creative yet affordable menu. Visit during the 33rd annual Gloucester Waterfront Festival (Aug. 17-18) for crafts, live music and food. Whenever you visit, tie up at Cape Ann Marina Resort (978-283-3293, capeannmarina.com), which provides transient dockage for vessels up to 150 feet.

Day 3: Newburyport, Massachusetts

The final destination of the weekend is Newburyport, a historic seaport 17 miles north of Gloucester that was the birthplace of the coast guard in 1965. Parker River National Wildlife Refuge is teeming with more than 800 species of birds, plants, and animals. Plum Island, 11 miles long, is great for birding and swimming. Hit Ten Center Street (978-462-6652) for a quick bite, especially if it's Wednesday, when oysters are $1. Michael's Harborside (978-462-7785, michaelsharborside.com) has great seafood and a lively outdoor bar. If you can, visit Newburyport during the annual Yankee Homecoming ( July 28“Aug. 4) for concerts, sidewalk sales, food vendors, and magnificent fireworks. Dockage is available at Newburyport Harbor Marina (978-462-3990, newburyportmarinas.com)

Related Articles
Orange Beach to Mobile, AL
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AS YOU AMBLE THE WHITE BEACHES of the Alabama Coast, you leave footprints on sands that once were the tops of the Appalachian Mountains. Transported south at the end of the last Ice Age, the sand is composed of pure white quartz crystals that create the legendary white sugar grains of Alabama beaches. A casual seaside village, an unspoiled natural island and a genteel cosmopolitan city thrive along the history-rich coastline.

Day 1: Orange Beach

A dynamic beach town surrounded by water in all directions, Orange Beach is a fishing wonderland nicknamed the “Red Snapper Capital of the World.” From the bayous to the reefs, and all the way out to the oil rigs, catches include several delicacies beside snapper. The abundance of fresh seafood dishes is found everywhere from shore shack to posh resort.

Unable to drag those toes away from the sand? Make tracks for The Gulf, a casual chic seaside hideaway with a unique shipping container design. Hang out at the bar or a communal table sipping and nibbling in the fragrant salty air.

For eclectic Southern and French-inspired dishes, head off the beaten path to Cosmo’s on Canal Road. Live music on the wooden deck makes Cosmo’s a happy hour favorite. Their Banana Leaf Wrapped Fish is on Alabama tourism’s list of “100 Dishes to Eat Before You Die.” Leave room for Soul Lovin’ Puddin’ or Peanut Butter Pie to finish.

Work off some of those Puddin’ calories on one of the 15 trails at Hugh S. Branyon Back Country Trail Complex. The hiking path winds among six distinct ecosystems within its 6,180 acres. For a more leisurely day, soak up the sunshine on one of the many public beaches.

Orange Beach Marina offers two retail stores and two award-winning restaurants. In a fully protected harbor off Terry Cove just minutes from the Gulf at Perdido Pass and the ICW, it accommodates yachts to 130 feet. Nearby Saunders Yachtworks is family-owned and offers a full-service boatyard.

Where to Dock: Orange Beach Marina

Day 2: Dauphin Island

Orange Beach to Dauphin Island — 28 NM

Source Trac3y on Flickr

As a barrier island, Dauphin is part of a complex estuarine environment that includes sandy beaches, tidal marshes and shallow lagoons rich in sea life. Attractions on the east end of the island include historic Fort Gaines, the Dauphin Island Sea Lab, Indian Shell Mound Park and Audubon Bird Sanctuary. On the west end are beautiful shimmering beaches, public golf courses and parks shaded by ancient oaks.

Dauphin Island is among the top four spots in North America for viewing spring bird migrations. A wide variety of species rest and recuperate on the 137 acres of the Audubon sanctuary whose unique geographic features include forests, marshes and dunes.

For thousands of years, the abundance of food, fresh water and other essential resources made this area a popular seasonal settlement for indigenous people. Indian Shell Mound Park is one of the best-preserved archaeological sites in the south. The mounds are believed to be the remnants of seafood meals consumed by Native Americans between 1100 and 1550. Today, Southeastern tribes maintain an ancestral connection to the ancient mounds’ original occupants.

A few blocks from the park is Light- house Bakery. Housed in an historic home, the front porch is a perfect setting for breakfast or one of their infamous cinnamon rolls with pecans. From there, it’s a short walk to The Hippie Fish boutique for not-too-touristy shirts and jewelry.

Any time of day is perfect for a smoothie, a fresh fruit bowl, an amazing waffle or ice cream at Foxy’s Waffle Bar and Sugar Den. Their motto: ALL CHILL! NO FRILL!

The sunsets on Dauphin Island are totally spectacular. View them from one of the local eateries or pick up the highly rated steamer pot from Skinner’s Seafood on Bienville Boulevard and dine on board as the sun sets.

The 235-slip Dauphin Island Marina sits at the base of Dauphin Island Bridge between the ICW and Mobile Bay. The full-service marina amenities include fuel, maintenance and a restaurant.

Where to Dock: Dauphin Island Marina

Day 3: Mobile, AL

Dauphin Island to Mobile — 27 NM

Mobile is one of America’s oldest cities, well known for its miles of streets canopied by majestic oaks. The city’s oldest living resident, the massive 300-year-old Duffee Oak, is just one of the city’s many centenarian live oaks. Beneath the hanging branches, large homes with sweeping front porches are adorned with hanging plants, swings and rockers with colorful pillows, and often a huge cat curled around itself.

Mobile celebrated the first Mardi Gras in the New World in 1703, long before the party began in New Orleans. Here it’s a family-oriented festival where Moon Pies are thrown along the parade route. Whether or not you’re in town for Mardi Gras, the Mobile Carnival Museum provides not only an excellent look into the history of one of the country’s oldest festivals, but also the design of the colorful costumes and the elaborate floats.

Beyond the usual must-see tourist stops—the blooms at Bellingrath Gardens, the retired battleship USS Alabama or the comprehensive GulfQuest National Maritime Museum— Mobile offers several unique adventures.

Dog River Marina | Tony on Flickr

Treasure hunters and bargain chasers flock to the 800 booths spread over 30 acres at the daily Mobile Flea Market. For genuine treasures, the Mobile Museum of Art houses more than 6,400 pieces of American, European and Asian decorative items ranging from contemporary artwork to classical antiquity.

Three centuries of ghosts, hauntings and dark secrets are woven into Mobile’s history. Hear tales of darkness, death and dismemberment on a Dark Secrets Tour of antebellum mansions, overgrown gardens and a church with a mysterious past. The historic Church Street Graveyard is considered one of Alabama’s most haunted cemeteries.

With so much cultural and ethnic diversity in its past and present, Mobile is an excellent place to gain an under- standing of life in the South during the Civil War era. Begin with a narrated tour of the Bragg-Mitchell Mansion, built in 1855. Then take the time to explore more than 40 stops along the Dora Franklin Finley African American Heritage Trail. The historical stories highlighted include early Creoles of color and survivors from the Clotilda, the last African slave ship to enter America in 1860.

Need a break from all the shopping, history and culture? Braided River Brewing Company offers a range of seasonal brews and limited releases. Or, spend the day along the miles of shimmering sand on Mobile Bay accompanied by a colorful beach umbrella and the latest mystery penned by a local author.

The downtown district’s historic buildings, fronted with lacy cast-iron balconies, surround shaded city squares. Art galleries, boutiques and eateries serving traditional Southern cuisine with a sophisticated twist are concentrated along Dauphin Street.

Tuck into A Spot of Tea for daily breakfast, lunch and brunch. While known for its Bananas Foster French toast, (another on one of the state tourism’s “Top 100” lists), the chicken salad is equally notable.

Just down the street is The Noble South, an airy eatery with whitewash walls and orange metal chairs. The brunch menu has irrestibles like Fig Crepes with maple syrup, lemon anglaise and honey roasted pecans.

NoJa, an inviting Mediterranian restaurant housed in an 1840s townhouse, offers seasonal dishes and scrumptious desserts including a Ginger Donut crowned with popcorn ice cream and caramel sauce.

For classic seafood such as shrimp etouffee and gumbo, try Wintzell’s Oyster House which began as a six-stool oyster bar in 1938 and is now a Gulf Coast tradition. Get in the spirit with their signature Dragon Drink, inspired by Vernadean, a beloved fire-breathing Mardi Gras float.

Where to Dock: Dog River Marina

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Spectacular Spans: A Tour of America's Great Bridges
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They come in all shapes and sizes, lengths and locations, ages and angles. For boaters, America’s coastal bridges are a fairly common sight, one that often goes unappreciated and undervalued, especially when most of us only get to see them up close from underneath — a unique perspective not often enjoyed by the general public.

Here are the stories of nine of our country’s famous bridges that span America’s frequently traveled waterways, along with fascinating facts that you can share as you sail under or drive over them.

Brooklyn Bridge

Perhaps the world’s most recognized span, this 139-year-old granddaddy of bridges took about 13 years to construct, linking Manhattan to Brooklyn and comprising the East River’s first fixed crossing. As the longest suspension bridge in the world when it opened in 1883, its main span measures 1,595 feet and deck rises 127 feet above the river’s surface.

Its building was a true family affair, designed by John Roebling who died unexpectedly after an injury he sustained in the early stages of the bridge’s construction. He was succeeded by his son, Washington who suffered a paralyzing caseof caisson disease. Unable to supervise construction in person, he directed the work from his nearby apartment using a telescope overlooking the site, while his wife Emily delivered handwritten instruction notes to the engineers.

Located between Piers 4 & 5 in Brooklyn Bridge Park on the East River is the new ONE°15 Brooklyn Marina with 100 slips for vessels up to 300+ feet. Estuary, the marina’s flagship restaurant, features new American cuisine, and the park is home to numerous restaurants, shops and cafes.

Chesapeake Bay Bridge (aka the Bay Bridge)

Soaring above Chesapeake Bay, this dual-span bridge connects Maryland’s densely populated Western Shore with the more rural Eastern Shore, running between Annapolis and Stevensville. The original two-way span opened in 1952; a parallel span was added in 1973 to alleviate congestion. It was only marginally successful.

Especially in summer, the bridge is often referred to as “the world’s tallest traffic jam,” packed bumper-to-bumper nearly 200 feet above the Bay. Because of its height, narrow spans, low guardrails and frequent high winds, the Bay Bridge is cited by some as one of the scariest crossings in America. But to west-bound travels, the sun setting over its tall towers and curved steel girders is a spectacular sight.

Located at the eastern base of the bridge on Kent Island is Bay Bridge Marina, which accommodates boats up to 70 feet. Sandy Point State Park Marina awaits on the westside for day use and fueling. Several other marinas are nearby.

Chesapeake Bay Bridge-Tunnel (CBBT)

Hailed as one of the great engineering marvels in the world when it opened in 1964, the original CBBT required the construction of four artificial islands, two miles of causeway, nearly six miles of approach roads, two-mile-long tunnels, four high-level bridges and 12 miles of trestle. It crosses the Chesapeake Bay between Cape Charles on the Delmarva Peninsula and Virginia Beach on the mainland.

The CBBT crosses two key East Coast shipping lanes. High-level bridges were initially proposed to span these channels, but the U.S. Navy objected to a bridge over one of the channels, because a collapse could cut off the Norfolk Naval Station from the Atlantic.

Cape Charles Yacht Center and Cape Charles Harbor Marina on the west side of the Delmarva Peninsula put you in the middle of the quaint shoreside town of Cape Charles and its charming shops, restaurants and accommodations.

Florida Keys Seven Mile Bridge

Among the world’s longest bridges when it was built, Seven Mile Bridge connects Knight’s Key in the Middle Keys to Little Duck Key in the Lower Keys. Actually two bridges, the newer span is open to vehicular traffic; the older is only for pedestrians and cyclists.

The older bridge was constructed in the early 1900s as part of the Key West Extension of Henry Flagler’s Florida East Coast Railway. After the Keys section of the railroad was damaged by the Labor Day Hurricane of 1935, Flagler sold it to the U.S. government, which convert edit to automobile use. Unsupported sections were added in 1935 to widen it for vehicular traffic, and the railroad tracks were recycled, painted white and used as guardrails.

Near the center, the bridge rises, providing a 65-foot clearance for boat passage in Moser Channel on the ICW. The remainder of the bridge is considerably closer to the water’s surface. Several marinas are on the Marathon end of the bridge.

Golden Gate Bridge

Named one of the Wonders of the Modern World by American Society of Civil Engineers, the 1.7-mile bridge was the world’s longest and tallest suspension bridge when it opened in 1937. Originally designed by engineer Joseph Strauss in 1917, the final design was conceived by Leon Moisseiff, engineer of New York City’s Manhattan Bridge.

The relatively unknown residential architect Irving Morrow designed many of the bridge’s Art Deco features, but his most famous contribution was its unique color, international orange. Others preferred that it was painted aluminum, dull gray, and the U.S. Navy suggested black and yellow stripes to ensure visibility by passing ships.

The water under the bridge is often turbulent, given the clash of the silt-heavy Bay waters and the cold Pacific Ocean currents. Consequently, recreational and commercial traffic are carefully monitored and regulated. Looking to dock and dine nearby? Try the north end of the bridge. Le Garage at Schoonmaker Point Marina in Sausalito serves innovative French cuisine, and at the casual eatery, Fish, place an order at the counter and sit at one of the picnic tables overlooking Clipper Yacht Harbor.

Mackinac Bridge

The engineering marvel often called “Mighty Mac” is the longest suspension bridge with two towers between anchorages in the Western Hemisphere, with a shoreline-to-shoreline length of five miles. Opened in 1957, it took three and a half years to build, because Michigan’s harsh winters limited construction to the summer months. Engineers faced daunting challenges. The Great Lakes freeze during the winter, causing large icebergs to place enormous stress on the bridge’s base.

The total length of wire in the main cables is an amazing 42,000 miles, enough to wrap around the Earth nearly twice. Painting the bridge takes seven years; when workers finish, they immediately start again. Locals note that the current in the Straits of Mackinac frequently changes direction, and when combined with wind-blown waves, churn from passing freighters and rebound off the bridge pilings, boating under and near the bridge can be challenging.

St. Ignace on the Upper Peninsula has a full-service public marina with 136 slips and is close to shops, cafes and restaurants, like the Mackinac Grille & Patio Bar.

Sunshine Skyway Bridge

One of Florida’s most iconic sights, the current Sunshine Skyway Bridge opened in 1987 and is the second bridge of that name on this site. The striking cable-stayed span connects the St. Petersburg peninsula to Terra Ceia, just north of Bradenton. The original bridge opened in 1954. A similar structure was built parallel and to the west of it in 1969 to make it a four-lane bridge.

In 1980, the freighter MV Summit Venture collided with one of the bridge’s supports during a storm, causing the
southbound span to collapse and sending vehicles into Tampa Bay. After the disaster, the northbound span was converted to carry one lane in either direction until the current bridge opened.

If you’re headed into Tampa Bay, Terra Ceia Preserve State Park is on your starboard side, a 2,000-acre mangrove forest and wetlands offering kayaking, fishing and nine miles of hiking trails. At the St. Pete end of the bridge, check out O’Neill’s Marina near Maximo Park.

Tacoma Narrows Bridge

The name Tacoma Narrows Bridge has been given to three different incarnations of this span connecting the city of Tacoma with the Kitsap Peninsula to the west. The original bridge opened in 1940 and spectacularly collapsed just four months later due to design flaws that resulted in what was termed “aeroelastic flutter.” It was replaced by the second Tacoma Narrows Bridge in 1950, which is still used for westbound traffic. A third parallel span opened in 2007 to carry eastbound traffic.

The collapse of the original bridge — nicknamed Galloping Gertie — had a major impact on the field of bridge aerodynamics, which influenced the design of all the world’s long-span bridges built since 1940. The newsreel footage of the collapse can still be viewed on
YouTube today.

Just south of the bridge you find Narrows Marina with transient docks that offer 375 linear feet of three-hour complimentary
guest side ties and 13 overnight moorage slips. The Narrows Brewing Company and Boathouse 19 restaurant are steps away.

Verrazzano-Narrows Bridge

This massive suspension bridge connecting Brooklyn and Staten Island opened in 1964 after decades of on-again off-again planning and five years of construction.
Each tower is made up of more than a million tons of metal, one million bolts and three million rivets. The four main suspension cables are 36 inches in diameter, and each is composed of 26,108 wires totaling 142,520 miles in length. Due to thermal expansion of the steel cables, the upper roadway’s height is 12 feet lower in summer than in winter.

The double-decker bridge carries 13 lanes of traffic, seven on the upper level and six on the lower level. Both the upper and lower roadways are supported by trusses that stiffen the bridge against vertical, torsional and lateral pressure — thanks to lessons learned from the Tacoma Narrows Bridge collapse in 1940.

Fort Wadsworth, at the Staten Island end of the bridge, is one of the oldest military installations in America, built in the early 1800s to protect the Narrows. In 1994, the U.S. Navy turned Fort Wadsworth over to the National Park Service.

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Chesapeake Bay Calendar of Events
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Summer is here, and it’s time to soak up the sun, visit bustling beaches, learn about boating history and relish the small-town charm around the Chesapeake Bay. Read on for hidden gems and tried-and-true events along the Bay, all the way from Havre de Grace to Cape Charles. Whether you’re a fan of watersports, arts and crafts, street festivals, or coastal cuisine, you’ll find something worth docking for a while.

July

Yorktown Farmer's Market/ Tony Alter on Flcikr

Yorktown Market Days, Fun in the Sun Market

Yorktown, VA

July 16 - Fun in the Sun Market;

August 6 - National Farmers Market Week

Experience a coastal Hampton Roads market on the York River. Check out local produce, meats, seafood, gourmet dog treats, art and more every Saturday this summer, and stop by one of the dates above for a themed, family-friendly extended market.

Where to Dock: Riverwalk Landing

Spirit of America

Havre de Grace, MD

July 2

Enjoy this beautiful town through a mid-century Americana lens at the Independence Day festival. You won’t want to miss the Patriotic Pooch contest, 50s throwback entertainers and best of all, derby races on Pennington Avenue.

Where to Dock: Tidewater Marina

Sea Glass & Beach Crafts Market at Annmarie

Solomons, MD

July 2

Kick off the holiday weekend at the Annmarie Sculpture Garden & Arts Center’s annual beach-themed market. Browse all things crafty and sea glass at over 50 booths!

Where to Dock: Solomons Harbor Marina

Kent County Waterman’s Day

Rock Hall, MD

July 3

For the first time since 2019, stop by and celebrate watermen who dedicate their lives to working on the Chesapeake! Enjoy a day of family fun, including anchor tosses and a raffle, culminating in the infamous boat docking.

Where to Dock: Haven Harbor Marina Resorts

Tuckahoe Steam & Gas Association’s 49th Annual Show

Easton, MD

July 7-10

Calling all car, truck and train enthusiasts! This multi-day show will be packed with steam and gas engines; antique tractors, trucks and cars; live steam train models; and even a horse pull.

Where to Dock: Easton Point Marina

Chesapeake Stand Up Challenge

Annapolis, MD

July 9 

Sponsored by the Eastport Yacht Club, this open water race has something for all levels. Experienced paddlers can fight it out in the seven-mile Challenge, and recreational paddlers will enjoy the 3.5-mile Challenge or one-mile Just for Fun race.

Where to Dock: Eastport Yacht Center

Plein Air Easton Art Festival

Easton, MD

July 17-24

Plein air painters express their craft from life instead of the studio, so you’ll see artists from across the country painting all around town. Also attend lectures and workshops, and buy art and other goods downtown all week. 

Where to Dock: Easton Point Marina

14th Annual Hampton Heat

Hampton, VA

July 23

Dock at the transient slips in downtown Hampton, then join the landlubbers at Langley Speedway, one of NASCAR’s best weekly tracks, for the annual Hampton Heat races.

Where to Dock: Bluewater Yachting Center

Southern Maryland Boat Club Bash on the Bay

Leonardtown, MD

July 29-31

Since the Calvert Marine Museum opened an exhibit on the golden era of powerboat racing in 2013, this vintage boat club has put on several races a year. Make your way to the historic Leonardtown Wharf to see vintage powerboats in action.

Where to Dock: Combs Creek Marina

2022 Snakehead Summer Slam

July 30

Annapolis, MD

Things are sure to heat up at the fourth of five tournaments in the 2022 Snakehead Championship Series at Anglers Sport Center. Anglers in kayak/shoreline and boating divisions will be up for all kinds of prizes, including one from the Coastal Conservation Association Maryland’s Great Chesapeake Invasive Count.

Where to Dock: Podickory Point Marina

Annapolis Yacht Club Two Bridge Fiasco Race

Annapolis, MD

July 31

Cruise to the southern Chesapeake to witness this pursuit style race starting between the Chesapeake Bay Bridge and Severn River Bridge. Look out for all types of boats in the competition, and even a foiler or two if you’re lucky.

Where to Dock: Annapolis Yacht Club

August

Annual Chesapeake Bay Balloon Festival

Cordova, MD

August 5-7

Embrace the Eastern Shore summer lifestyle at this family-friendly festival. Feel the adrenaline rush of hot air balloon rides and keep the thrill going on the mechanical bull and bouncy house on land.

Where to Dock: Easton Point Marina

A Day of Celebration & Remembrance of Harriet Tubman

Cambridge, MD

August 6 

Celebrate Harriet Tubman’s life, bicentennial and antislavery activism on the Underground Railroad just miles from where she lived as a child. Join the commemorative parade through the streets of Cambridge and enjoy local vendors and entertainment at the festival.

Where to Dock: Cambridge Yacht Basin

Pirates & Wenches Weekend

Rock Hall, MD

August 12-14

Presented by Main Street Rock Hall, you can dock at a local bayfront marina ready for an immersive, family-friendly weekend. The whole family will love the marketplace on Main Street, pirate and mermaid performers, and costume contests, and there will be no shortage of grub and grog.

Where to Dock: Haven Harbor Marina Resorts

Solomons Dragon Boat Festival 2022

Solomons Island

August 13

Cruise to scenic Solomons Island to watch 30 dragon boat teams compete for glory on the Patuxent River and explore the local vendor village. Arrive the week before and you might catch a Dotting of the Eye Ceremony or even a flash mob.

Where to dock: Solomons Harbor Marina

Leo Wardrup Memorial Cape Charles Cup Regatta

Cape Charles, VA

August 20-21

Make your way to Virginia’s Eastern Shore for two days of racing on the Chesapeake. While you’re there, lounge on the Cape Charles town beach, stroll around the retail district and check out Victorian homes in the historic district.

Where to Dock: Cape Charles Yacht Center & Marine Services

7th Annual Coastal Craft Beer Festival

Virginia Beach, VA

August 27

Spend your Saturday at the waterfront Neptune’s Park, tasting your way through 60+ beers, ciders and seltzers from 30 breweries. Learn about all Virginia breweries have to offer or branch out with some regional or national craft brews.

Where to Dock: Rudee's Inlet Station Marina

September

The Waterfront Festival

Havre de Grace, MD

September 9-10

Cruise to the northern Bay to round out your summer with this annual festival, kicking off with a lighted boat parade. Enjoy fun for the whole family with fresh crab and seafood, beer gardens, live music, hot air balloons and a youth fishing derby!

Where to Dock: Tidewater Marina

2nd Annual Portsmouth Paddle Battle

Portsmouth, VA

September 10 

Whether you kayak or paddleboard as a novice or a pro, or enjoy waterfront live music, food and drink, there’s a place for you in the Paddle Battle on the Elizabeth River. Proceeds will support the Portsmouth Naval Shipyard Museum and Lightship Portsmouth Museum.

Where to Dock: Tidewater Yacht Marina

TrawlerFest Baltimore

Baltimore, MD

September 27-October 1

Close out your summer season with Passagemaker’s annual boat show held at Harbor East Marina in the heart of downtown Baltimore. The show hosts impression in-water selections of new and pre-owned long-rang cruisers, coastal cruisers and of course, tons of trawlers. Free seminars and educational demonstrations are held throughout the weekend.

Where to Dock: Harbor East Marina

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