Wednesday, April 19, 2006

Side trips: Maryland's Eastern Shore


Contributed by Cathy Jordan

Life on Maryland’s Eastern Shore ranges from active rural farms to manufacturing plants to the beaches at Ocean City and the ponies at Assateague Island State Park. Separated from the rest of Maryland (except at the north end) by the Chesapeake Bay, this peninsula has much to see and do. To get here, follow the directions to get to Annapolis (see the entry for Annapolis on this blog), but instead of getting off Route 50, stay on Route 50 crossing the 4.5 mile long Chesapeake Bay Bridge (toll).

Here are a few places to check out on the western part of the Eastern Shore:

EASTON (located just off Route 50)

This small, historic town (founded in 1711) has been named the “8th Best Small Town in America”. It has many great examples of colonial and Victorian architecture, unique shopping, and fine restaurants. One way to see Easton is to take their self-guided walking tour – you will see such historic buildings as Christ Church (built 1840-44) (, the Third Haven Friends Meeting House (this Quaker church was built in 1682, and is considered to be the oldest documented building in Maryland) (, the Talbot County Courthouse (originally built in 1712) (, the James Neall House (1810) and the Joseph Neall House (1795).

Restaurants to try out are:

Inn at Easton 28 S. Harrison (

Mason’s 22 S. Harrison (a restaurant and gourmet deli)

Restaurant Columbia 28 S. Washington (located in a 1795 house)

Legal Spirits Tavern 42 E. Dover St. (“a must stop for the soup”, “the local’s favorite”)

Chez LaFitte 13 S. Washington (a cafe and piano bar) – they have psychic readings on Sunday evenings. (

Bed & Breakfasts:

Bishop’s House Bed & Breakfast, 214 Goldsborough St. This is an 1880 Victorian home; 2-night minimum required.

Chaffinch House 132 S. Harrison St. This is an 1893 Queen Anne Victorian.

Inn at Easton 28 S. Harrison. Restaurant and Inn.

Unique shopping opportunities abound! In addition to many antique shops, the choices include the Wood Duck Shoppe & Gallery (waterfowl decoys, carvings, etc.), Yarns (yarn and needlecraft), M. Randall & Co. (sweaters), and Crackerjacks (unique toys & games for all ages).


Turn off Route 50 just prior to reaching the main part of Easton onto Route 33 and you’ll come to this quaint (and very popular), waterfront village along the Miles River. This town was founded in 1631 and held off the British during the War of 1812 by devising a blackout in the town. James Michener lived here while he was writing his novel, Chesapeake.

St. Michael’s also has a self-guided walking tour – among the sites you will see are St. Mary’s Square (founded in 1778), the Cannonball House (the only house struck in St. Michael’s in the War of 1812), Christ Episcopal Church (the original building went up in 1677), and many historic homes.

One of the main attractions in St. Michael’s is the Chesapeake Bay Maritime Museum (at the end of Mill Street). The museum has 10 exhibit buildings, the historic Hooper Strait Lighthouse (yes, you can climb all over it), and a working boat yard. It is open from 10AM-6PM daily and costs $10. ( You may also want to consider a boat ride on the Miles River – Patriot Cruises (berthed at the Maritime Museum) offers 60 minute or 90 minute narrated tours – you may see waterfront mansions, osprey nests, and more. (

Restaurants to try:

The Crab Claw – very popular restaurant on the waterfront. It has both indoor and outdoor seating, but is well known for their “table full of crabs to crack open”! Located at the end of Mill Street near the Maritime Museum. (

Town Dock Restaurant (125 Mulberry St.) – this is also a waterfront restaurant a bit more upscale than the Crab Claw. (

Bistro St. Michael’s, “a re-creation of a classic French bistro” (403 S. Talbot – the main street through town). (

Bed &Breakfasts:

Cherry Street Inn , 103 Cherry Street (

The Snuggery, 203 Cherry St.. Original log house was built in 1665; logs recently revealed in a renovation.

Wades Point Inn on the Bay, Wades Point Road. Waterfront inn on the road to Tilghman Island. (

Shops in St. Michael’s include:

A Wish Called Wanda (110 N. Talbot) has handcrafted Blue Crab pottery, jewelry & giftware,

Flamingo Flats (100 Talbot) is a specialty food store,

Sign O’the Whale (108 S. Talbot) has an unusual selection of tableware, garden & kitchen items, and Harbor Sweet chocolates; one of my favorite stores!,

Simpatico (104 Railroad Ave) has Italian ceramics, linens, etc.,

Mind’s Eye Gallery (205 S Talbot) has handcrafted items from over 200 artisans – another of my favorite stores!


Tilghman Island, 12 miles South of St. Michael’s on Route 33, is separated from the mainland by Knapps Narrows and is accessed by drawbridge. This working watermen’s village, surrounded by the Chesapeake Bay, is home to the last commercial sailing fleet in North America – the skipjacks. The skipjacks are on display at Dogwood Harbor. Tilghman Island was founded as a land grant in 1659 – it was then called Great Choptank Island, and is only 3 square miles. There are several historic homes here as well as the historic St. John’s Chapel, built in 1891.

There are 2 boat tours you may be interested in taking:

Skipjack Tours ( provides a 2 hour cruise on the working skipjack, the Rebecca T. Ruark,

Lighthouse Cruise Tours ( – this company has 3 Chesapeake Bay lighthouse tours, all leaving from Dogwood Harbor on Tilghman Island – they include 10 lighthouses, 5 lighthouses, and a sunset cruise with 2 lighthouses.

Restaurants to try:

Bridge Restaurant, 6136 Tilghman Island Road – waterfront (

Harrison’s Chesapeake House Country Inn, 21555 Chesapeake House Drive (this is also a B&B) (

Tilghman Island Inn, 21384 Coopertown Road – waterfront. (

Bed & Breakfasts:

Black Walnut Point Inn, Black Walnut Point Road (

Sinclair House Bed & Breakfast, 5718 Black Walnut Point Rd, (

Lazyjack Inn, 6907 Tilghman Island Road (


Oxford, Maryland, founded in 1683, is on the Tred Avon River near the Choptank River where it enters the Chesapeake Bay. Oxford today is still a watermen’s town, but is enjoying a new resurgence based on tourism and leisure activities. Its quiet charm, fresh air, summer breezes, and clean water provide a haven from the hustle and bustle of city life for boaters, weekend visitors, and summer residents. Homes proudly display when they were built. Walk along The Strand, a waterfront walkway, or have a picnic at Town Park.

Some things to see or do:

Oxford Custom House (next to the ferry landing) is a replica of the original that served during colonial times. Open on weekends.

Oxford Museum (100 S. Morris St) contains arrowheads, duck carvings, ancient ship logs, lighthouse lamps, a 1950s ice cream parlor, and gift shop. (

Cutts & Case Shipyard (306 S. Tilghman) – this company makes wooden boats the old-fashioned way and offers tours of their shipyard. (

Channel Charters offers historical cruises on the Satisfaction; the cruises highlight the town’s history, celebrated citizens, and notable structures.

Restaurants to try:

Latitude 38 (26342 Oxford Rd) – highly recommended (

Oxford Market & Deli (203 S. Morris) – home of the Oxford pies.

Robert Morris Inn, (310 N. Morris), built in 1710. This is highly recommended by one of my coworkers.

Shops –

Americana Antiques (111 S. Morris) includes wood-carved carousel horses

Oxford Mews (105 S. Morris) is like an old general store; it carries “necessities, gifts, and non-essentials”

Pope’s Treasures (506 S. Morris) carries local artwork and nautical gifts.

Bed & Breakfasts –

Oxford Inn (506 S. Morris) , built in 1900, has harbor views. (

The Nichols House (217 N. Morris) has a private cottage and Victorian garden (

The Combsberry (4837 Evergreen Rd) is in the style of an English country mansion; built in the 1730s. (

Ruffled Duck Inn (110 N. Morris) is a Victorian B&B (

To get to this small town, turn left off Route 33 (on your way to St. Michael’s) onto Bellevue Road. At the end, you will reach the Oxford-Bellevue Ferry, which crosses the Tred Avon River from Bellevue to Oxford. This is the oldest continuously operating ferry in the United States, starting in 1683; the route is ¾ mile and takes 10 minutes one-way, hold 9 cars plus walk-on passengers. (

Updated 5/2/06: The original text had codes copied from wordprocessing software that broke the feed. Formatting removed.


Anonymous Anonymous said...

Does anyone know of a shuttle or bus service that goes to Assateague Island? I'll be in Baltimore sans vehicle, but I'd really love to get out to see the famous ponies. Any information you could post would be very much appreciated! Thanks!


4/22/2006 5:14 PM  
Blogger Christina said...

Hi E-
We don't know of any regularly scheduled buses to Assateague -- it's about a 3 hour drive so you might want to rent a car. Sorry!

4/25/2006 5:23 PM  

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