Holiday charm in seaside St. Michaels

St. Michaels, Maryland is just about halfway between Cape Cod, Massachusetts and Key West, Florida, in every possible way.

This waterfront vacation town situated on the Eastern Shore of the Chesapeake Bay mingles the Florida Keys’ laid back vibe with the Cape’s sailboats and seersucker shorts. Art galleries, wine shops and boutique restaurants lounge beside souvenir stores and old-time ice cream parlors. Tiki bar bartenders sling fruity rum cocktails to partying tourists, while at the same time a couple exchanges vows in a quaint, waterfront wedding ceremony at the upscale resort across the harbor. 

Located about an hour and a half drive from either Baltimore or Washington, D.C., St. Michaels is a go-to destination for regional vacationers. The look and feel resembles a tropical version of a New England coastal town, seamlessly melding together aspects of both locales into a mid-Atlantic waterfront respite.

For Cape and Keys frequenters, the similarities begin before you even arrive. Weekend traffic on the Chesapeake Bay Bridge would make anyone who has ever crossed onto Cape Cod – or any other beach destination – shudder. The sheer size of the bridge makes it as much a modern engineering marvel as the Seven Mile Bridge the traverses the Florida Keys.

In culinary terms, Maryland is known for crabs in the same way that New England is for lobster and the Florida Keys are for fresh fish. There is no better way to get a flare for the Eastern Shore than to partake in a crab feast along the water, and there is no shortage of quality establishments. For years St. Michaels Crab Claw restaurant and St. Michaels Crab and Steak House – located directly across the harbor from one another – have been serving up local seafood and the hallmark Maryland blue crabs.

For the uninitiated, a crab feast is similar to a lobster bake in that work is involved. One typically begins with a table wrapped in paper, which is promptly covered with the cooked crustaceans. Steamed and covered in mounds of Old Bay seasoning, they are simply prepared. A small mallet, paring knife and placemat instructions will get you to the best bits. The sweet, familiar shellfish flavor skews unique with the abundance of salty seasoning.

Like many typically summer destinations, St. Michaels’ crowds clear in the off-season. But tasty wood-fired pizzas at Ava’s (409 South Talbot Street), and the perfectly executed entrees at 208 Talbot (208 Talbot Street), mean food is plentiful and high quality any time of year here.

With an annual oyster festival and holiday events throughout the season, the town will impress curious visitors looking for a November or December getaway. On December 7 the town shops open late for “Midnight Madness,” drawing locals and visitors alike out into the streets to enjoy snacks, singers, prizes and of course, sales. December 13 – 15 marks the annual “Christmas in St. Michaels” festival, featuring parades, music and tours of some of this historic town's antique homes (for more info visit www.stmichaelsmd.org).

Where St. Michaels hovers in between its northern and southern cousins, it ascertains one aspect of seaside living that sets it apart – the sunset.

Perching along the right Massachusetts inlet or cove will provide a spectacular view of the setting sun. In Key West there is an entire pavilion at the end of the town’s famed Duval Street dedicated to street performers celebrating the stunning sunset view each night. St. Michaels may just outdo them both.

A few minutes out of the town center, Wades Point Inn on the Bay (www.wadespoint.com) guards the elbow of this L-shaped peninsula. A tree-lined gravel road opens into a sprawling green lawn stretching in almost all directions to the water’s edge. At the center stands a grand, whimsical 1819 Georgian-style manor house wrapped in multi-level porches. The main house offers three floors of quaint, bed and breakfast rooms while an adjacent building constructed in the 1990s has more family-friendly accommodations.

Waking up at Wades Point means homemade breakfast made from local ingredients, like scrapple or eggs from down the road. But day’s end is the Inn’s best selling point, and one of St. Michael’s best treasures.

The savvy visitor will have filled a hammock, staked out a lawn chair or a spot on the dock well before dusk, perhaps with a bottle of wine from the local St. Michael’s Winery (609 South Talbot Street). Wades Point staff will happily provide wine glasses and a corkscrew.

Any spot affords a breathtaking panorama of the bay. The sun sets straight on, sinking down behind a wisp of land across the Chesapeake just large enough to mark the split between sea and sky. It washes the entire yard in surreal colors: orange, pink and purple light, reflecting off the water and the manor house’s white exterior. Serenity and scenery are one in the same.

St. Michael’s may resemble the best of the Cape and the tropics, but it certainly has a charm all its own.