Off-the-Beaten Track Mother/Daughter Getaway To St. Michael’s on Maryland’s Chesapeake Bay

Five Gables Inn & Spa is great place to explore charming town.

By Karen Rubin and Eleanor Rubin

I’ve been intrigued about Maryland’s Chesapeake Bay area ever since reading James Michener’s epic novel, “Chesapeake.” So, when we arrived in St. Michaels for a mother/daughter getaway to the Five Gables Inn & Spa, I was delighted to find several locals whose stories found their way into the novel, and who had a few more to share of the time spent in his company.

Michener, who lived here in the early 1970s and published his novel in 1978, probably would not recognize St. Michaels, since his novel contributed to the village’s renaissance, though the revival had already been set into motion with the founding of the Chesapeake Maritime Museum here in 1965. Still, I am sure, many aspects remain the same, and are the very source of its appeal-the charming, tree lined streets of 1800s houses, the skipjack boats for oystering and scores of every other type of sailing and motoring vessel and yacht that float into the harbor, and now, an entire industry of clever, upscale boutiques and shops, cafes and restaurants.

St. Michaels, which has been drawing people since the birth of the colonies, is being rediscovered. Real estate offices and contracting companies are as plentiful as bed-and-breakfasts now, and every where you go, historic homes are being renovated-between the visitors who come for a dose of r&r and now provide traffic for the bnb’s, and those who found they can live here and telecommute or somehow fashion a living here so purchase their own.


Located in the center of a special watery world on Maryland’s Eastern Shore, and nestled between the Miles River on the north and Broad Creek and Harris Creek to the south, it is a collage of historic homes, southern culture, and a proud maritime history.

St. Michaels is a popular getaway for Washington, Baltimore, Annapolis and Philadelphia which are about two or three hours away by car, and especially for those who come by boat. They not only come for boating and sailing and fishing, as well as hunting in season. Indeed, St. Michael’s has been hunting grounds for the Native Americans who lived in the area, who, according to a local woman who has traced her ancestry back to the earliest white settlers here, lived peacefully together.

St. Michaels, though, is off-the-beaten track from our area, and getting there, takes you through some beautiful cornfields and farmland such as has all but disappeared from the landscape of our travels. Even if you come for a brief sojourn, you feel as if you have really gone far away.

People talk to you in St. Michaels. Strolling around one charming street, admiring the 1800s architecture, a man sitting nonchalantly on his porch chimed in to our conversation and told us the story of why St. Michaels is “The town that fooled the British.” Another woman, who has traced back 12 generations of her family in St. Michaels, related that Donald Rumsfeld has purchased a place in town and was seen playing pool with Colin Powell above the Carpenter Street Saloon.


It is a charming village, with just about everything in walking distance. Because of the small scale, it is very relaxing and you feel yourself decompress as you casually wander about. And for our mother/daughter getaway, St. Michaels and the Five Gables Inn was perfect.

Five Gables Inn & Spa

The Five Gables Inn & Spa is distinguished because of the spa and a gorgeous indoor pool (the floor-to-ceiling mural is fabulous). The inn offers 14 rooms in three circa 1860 homes-two adjoining traditional Brick and the colonial-style Five Gables located across the street. The properties have all been renovated and offer an elegant (not too cutesy) and comfortable getaway.

Each of the 11 rooms and 3 suites is individually decorated, and feature working gas fireplace, antique furnishings, Jane Wilner toile linens, Frette towels and down comforters. Our room was one of several that had a private balcony or porch. In-room amenities also included color TV with cable and VCR (a selection of movies is available to guests), CD player, hair dryers, irons, and plush robes. The bathrooms all feature single or double whirlpool tubs and Aveda products.

A lavish continental breakfast is served daily in an extremely pleasant breakfast room-homemade breads, muffins, pastries, cereal, yogurt, fruit, assorted juices, coffee and tea; in addition, afternoon refreshments are available at 3 p.m.


It is notable that this is a pet-friendly property (its shop across the street, Flying Fred’s, is an upscale pet boutique that sells clothing, treats, special toys, collars, leashes, and also a collection of artwork from Stephen Huneck); with advance notice, dogs are welcome for a charge of $35 per stay, and receive the use of a dog bed, special fuzzy toy, and doggie treat.

A centerpiece is its full-service Aveda concept Spa, which aims to enhance relaxation of body, mind and spirit, and stimulate, nurture and educate guests. The Aveda products used are formulated with pure flower and plant essences. There are four multi-purpose rooms, one hydrotherapy room, one couples treatment room, a heated indoor pool, steam room, sauna. The Spa’s sea green walls are adorned with vintage French posters.

Treatments available include herbal hydrotherapy bath utilizing blends of Aveda aromatic herbs to relax muscles ($25/20 minutes); massage therapy ($70/45 minutes); facials ($100); rosemary mint awakening body wrap ($140/90 minutes); enlivening back treatment ($90/45 minutes); body polish ($140/90 minutes); “The Ultimate,” including hydrotherapy bath, 30 minute facial and one hour massage ($170); “The Indulgence, consisting of 30 minute facial and Rosemary Mint Wrap or Body Polish ($195/125 minutes); and “The Luxurious,” combining one-hour facial, one-hour massage, and choice of wrap or body polish ($295/215 minutes).

The inn also makes bikes available to guests, which I happily used to explore. In this way, I came upon the local museum, and a cannon dating from the Revolutionary War, and another from the War of 1812.

It was the War of 1812 that provided St. Michaels’ claim to fame. In 1813, a number of British barges had planned an attack on the town of St. Michaels and a fort on the harbor side. The residents, forewarned, hoisted lanterns to the masts of ships and in the tops of trees, tricking the British by causing the cannons to overshoot the town; only one house, known today as The Cannonball House, was struck. Thus, the moniker, “The town that fooled the British.” The local gent, though, retold the legend but added his own belief that the British weren’t entirely fooled; rather, they never intended to bomb the village but were aiming instead where they thought the militia was based.

The Five Gables Inn proprietors are John and Bonnie Booth. John spent two years in the Navy and 16 in Wall Street before beginning his own construction company. He announced one day that they were moving to St. Michaels, where he renovated old homes and kept his own eye on a historic brick building in a prime main street location. When it came on the market in 1992, he purchased it, renovated it, called it The Brick House, and helped Bonnie open a fine needlepoint store called B’s Stitches; a year later, he had two guest rooms above the store that he rented to travelers on weekends, and would bring breakfast form his home four miles away. He purchased the building next to the Brick House, joined them together to create an eight-room bed and breakfast. Next, they were able to purchase the stately, colonial-style white house across the street, which they renovated and renamed Five Gables. After a visit to Lavender Hill Spa in Calistoga, California, they decided to open the spa. The Inn is now managed by veteran innkeeper Marianne Lesher.

In addition to the pool, spa, and bikes on property, tennis, golf, sailing, hunting and fishing are located just minutes of the property.

Area Attractions

A highlight of our visit to St. Michaels was the visit to the Chesapeake Bay Maritime Museum. Situated on the 18 waterfront acres in the historic district, the museum brings to life the story of the Bay and the people who have lived around it-particularly the people of the oystering industry (though the museum could do a better service to the Native Americans)-and the environmental threats to the region. It traces the geological, social and economic history of the Chesapeake Bay through the age of sail and the steamboat era to the advent of the gasoline and diesel-powered engines, all the while showing how new technology displaced old and changed society.

There are 35 buildings, 10 of which house exhibits that are open to the public, including a phenomenal display of the golden age of steamboats, and the world’s largest collection of traditional Bay boats (like the skipjacks), and another distinctive exhibit about waterfowl hunting. You can watch boat builders-on weekends, “apprentices” join master shipwrights and you can purchase the result: $3,500 for a shell, and $6,500 for a sailing skiff).

The best part of the museum was the fully restored 1879 Hooper Straight Lighthouse, which you can climb to the very top and see the light, as well as visit the various rooms with artifacts which are revealing about the keeper who would have lived in isolation for all but 5 days of the month.

The Chesapeake Bay Maritime Museum, which will engage youngsters and oldsters alike, is open year round (except major holidays), and offers special events (an Oysterfest in November, for example), plus educational programs, lectures, concerts, and cruises. (Chespeake Bay Maritime Museum, Navy Point, 410-745-2916,

The museum also offers a self-guided walking tour, so as you stroll about, you can find out about the history of some of the homes.

Visiting the museum will undoubtedly fill you with the desire to take to the water yourself, and there are many choices. Captain Ed Farley, an oysterman, takes up to 32 guests at a time on his working skipjack, the H.M. Krentz, for a two-hour sail. Built in 1955, the H.M. Krentz is one of the last commercial sailing vessels that continues to dredge oysters in the Chesapeake during the winter (the ship is also available for charter) (three sails a day, $30/adults, $15/child; 410-745-6080).

There are also sailing charters on the Footloose yacht (443-822-5791); and a 36-foot catamaran, the Sirius, (410-745-6203, You can also participate in a hands-on sailing adventure onboard the oldest working skipjack, the 52-foot Rebecca T. Ruark, a National Historic Landmark built in 1886, to learn about ecology and maritime history (410-829-3976, Guided flyfishing excursions are available through the Keeper-Orvis shop in town.

You can also go on a tour of 10 different lighthouses, through Chesapeake Bay Lighthouse Tours, by water (800-690-50800,

Another activity is to take a ride across the bay’s inlet to Oxford, Maryland, on the oldest car ferry on the East Coast. Family-owned and operated since 1683, the Oxford-bellevue Ferry takes travelers on the 10-minute ride to Oxford, one of the ooldest towns in Talbot County and the first and only port of entry on the Eastern Shore, where you can see late 17th century homes and specialty shops.

We were so enamored with the harbor, we selected a delightful casual place to eat, the Crab & Steak House. Another tradition in St. Michaels is the Crab Claw, next door to the museum, famous for steamed Maryland blue crabs for more than 50 years, which we also enjoyed.

St. Michaels also hosts an enormous number of festivals all during the year: “Fall into St. Michaels” in October; Oyster Month in November; “Christmas in St.Michaels, form Dec. 13-14 with parade, Santa’s wonderland, tour of homes and live music.

The Five Gables Inn has created some wonderful packages, that feature the spa, sailing, golf, romance.

A new Five Gables “Golf & Spa Package,” available June through September 31, is a two-night midweek package that includes one tee time, a 30-minute facial, one-hour massage and a Rosemary Mint Body Wrap; if both partners are golfers, the package includes tee times for two, an herbal bath each and one hour couples massage. Guests also receive a gift of three golf balls and tees. Guests play at the nearby Harbourtowne Golf course, designed by Pete Dye. The package begins at $665 per room, based on double occupancy.

Its signature two-night “Spa & Sail Package”, available from May through mid-November, includes a two-hour sail aboard the Rebecca T. Ruark, the oldest working skipjack in North America; dinner at The Crab Claw Restaurant; and one-hour massage per person. Double occupancy rates begin at $550 midweek and $750 on weekends.

Five Gables Inn & Spa, 209 North Talbot Street, St. Michaels, MD 21663; 877-466-0100,,

For information on St. Michaels, contact the St. Michaels Business Association, PO Box 1221, St. Michaels, MD 21663, 800-808-7622,
© 2005 Travel Features Syndicate, a division of Workstyles, Inc. All rights reserved. Send comments or travel questions to

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Karen Rubin is an eclectic travel writer who has been spanning the globe for more than 30 years reporting on interesting, intriguing people and places to explore for magazines, newspapers and online. She publishes Travel Features Syndicate in newspapers and online including, Huffington Post and and blogs at "Travel is a life-changing and an interactive experience that mutually benefits travelers and community." Contact Karen at 'Like' us at

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