A red bicycle near the rear porch of the Bishops House

5+ Day Itinerary

Day One

If you are beginning your vacation in Easton, MD

Welcome to Easton, Maryland ranked eighth in the book “The 100 Best Small Towns in America”. Easton, known as “The Colonial Capital of the Eastern Shore”, grew inward from the water, growing around a religious institution, Third Haven Meeting House, circa 1682; and a court of justice, Court House, circa 1711.

Be sure to visit Easton’s Farmers’ Market on Saturdays from 8 AM – 1 PM, located on Harrison Street. The market offers the freshest local produce and many crafters offer their special wares for sale (April-December). Enjoy live music performed by local talent on Saturdays beginning at 10:30 AM.

Eating Easton – Late Saturday Mornings. The Eastern Shore’s premier three hour food tour group. Join us on our adventures inside the restaurants that have impacted Easton’s culinary scene. You will taste food from Easton’s top chefs and learn what inspired them to call this historic town their home. The three hour tour features: a bit and sip at a minimum of four amazing restaurants, behind-the-scenes access to Easton’s food culture; specialty alcoholic or non-alcoholic pairings, a visit to a distinctive culinary shop, and educational and delectable experience. Tours begin at the Avalon Threatre. Advanced reservations required. Tickets are $59 per person for all food, beverage, and guidance. E-mail: info@eatingeaston.com or 410-635-4130.

Take a self-guided tour of the historic district of Easton offering a wide range of architectural styles from Federal period to fine Victorian (tour maps available at Easton’s Welcome Center on Harrison Street or Click to download a PDF file of the historic Easton walking tour). Or, begin your tour with a stop at the Talbot Historical Society, 30 Washington Street. The Society offers over 1,000 vintage photos telling the fascinating story of Talbot County and its people and special exhibits featuring life on the Eastern Shore. The Talbot Historical Society maintains a museum, award-winning Federal-style gardens, (open daily), and a unique consignment shop entitled Tharpe House Antiques. The Museum, located in the Mary Jenkins House is open Thursday, Friday and Saturday 10 AM – 4 PM. The Galleries at Neall House is open on Saturdays from 10 AM – 4 PM beginning April 1 through December. 410-822-0773.

Guided Easton Walking Tours depart from the Tidewater Inn or from your location in downtown Easton. Tours are led by a local historian with ten years of experience in Talbot County history. Tours can be designed with consideration to personal/special interests. Available by reservation only. Admission charge $20 per person. https://walkingtourstalbot.wordpress.com

Easton is also recognized as one of the “100 Best Small Arts Towns in America”. You’ll see part of the reason why when you visit The Academy Art Museum. Located at 106 South Street, the Academy houses a permanent collection of works (1,000 pieces), by prominent 19 & 20th century artists, regularly hosts special traveling exhibits and a rotating exhibition program featuring local, regional and nationally respected artists. Open Monday, Friday, Saturday & Sunday 10 AM – 4 PM, Tuesday, Wednesday & Thursday 10 AM – 8 PM. First Friday of each month 10 AM – 7 PM. Admission $3 pp

Easton offers a variety of dining experiences for lunch. Dine indoors or out or utilize the many carry-away facilities offered in the community for picnicking in Idlewild Park, Thompson Park, or Talbot County Courthouse Grounds.

Spend the afternoon browsing the many art galleries, boutiques, specialty, and antique shops in town or on adjoining Route 50 (Ocean Gateway Highway) Town Center shop hours Monday – Friday 10 AM – 5 PM. Art galleries offer extended hours on the First Friday of each month for First Friday Gallery Walk. Boutiques and specialty shop hours vary on Saturday and Sunday. Easton provides the most exciting opportunities for antiquing on the eastern seaboard. From elegant 18th century furniture to oriental rugs and Chinese porcelain, glass, and pottery to “country” collectibles and decoys, treasures abound for every taste and budget.

If outdoor recreation is on your agenda, Easton has a public championship golf course within minutes of Town Center, Hog’s Neck Golf Court, Old Cordova Road, 410-822-6079, offers both an 18-hole championship course and a 9-hole executive course.

If you are a runner or walker, Easton’s Rails to Trails offers hard topped and a level surface for your walking or jogging pursuits. The trail is located next to the restored Easton Train Station at Goldsborough Street and Railroad Avenue and continues to the Easton’s Sports Complex off Route 50, (approximately 1 mile), or in the opposite direction to Idlewild Park, approximately 7/10s of a mile. The Rails to Trails is also an excellent choice for a short bike trip through Easton’s residential communities.

Public tennis courts are located at Idlewild Park, Washington and Aurora Streets, and the YMCA, 202 Peachblossom Road, 410-822-0566, welcoming visitors to their courts.

Kayak rentals are available at Easton Cycle and Sport, at 723 Goldsborough Street, Easton, 410-822-7433, stand-up paddleboards, or a Hobie Cat sailboat, with all the equipment and accessories for a safe and comfortable outing including delivery to you. Bicycle, kayak and stand-up paddleboard rentals plus guided tours through St. Michaels are available at two locations in St. Michaels on Mulberry Street and 500 South Talbot Street, 410-745-2320, from Shore Pedal and Paddle.

The Country Comfort Farm, located on St. Michaels Road, offers horseback riding at its finest. The facility boasts both indoor and outdoor arenas with 70 acres for trail rides and experienced staff and equines. Advanced reservations are required and may be made via e-mail: nfaulkner@bluecrab.org or by phone, 410-745-3160.

Talbot County Department of Parks and Recreation offers two Outdoor Community Pools for swimming. The George Murphy Pool, located at 510 Port Street & Easton Bypass at Moton Park in Easton, 410-820-7306; and the Bay Hundred Community Pool at 911 S. Talbot Street in St. Michaels, 410-745-6592. The pools are open Memorial Day Weekend to Labor Day Weekend from Noon-7 PM. Daily admission fees are $2-$3 per person. The local sandy beach area is at the end of the Strand, (Tred Avon River Walk), in Oxford.

Pickering Creek Audubon Center offers Guided Walks on the 1st & 3rd Sundays of every month, April thru May at 2 PM, June thru August at 9 AM and September thru November at 2 PM, 410-822-4903. Canoes may also be rented at Pickering Creek with a nominal membership fee.

The Blackwater National Wildlife Refuge in Dorchester County offers three paddling trails through a watery wildlife wonderland. Canoe/kayak rentals are available from the following outfitter: * Blackwater Paddle and Pedal Adventures, 4303 Bucktown Road & 2524 Key Wallace Drive – 410-901-9255, (Closed Sundays). Maps and guides of the trails may be purchased at the Blackwater NWR Visitor Center or by contacting Friends of Blackwater 410-228-2677. The Refuge includes over 27,000 acres, composed mainly of rich tidal marsh characterized by fluctuating water levels and varying salinity. Other habitat types include freshwater ponds, mixed evergreen and deciduous forests, and small amounts of cropland and managed impoundments that are seasonally flooded for waterfowl use.

Indoor health and fitness centers offer a broad range of fitness and state of the art cardiovascular equipment. These include the YMCA, 202 Peachblossom Road, 410-822-0566 and Hearthstone Health & Fitness, 8632A Commerce Drive, 410-690-3838.

After lunch, travel to Oxford. Oxford is an oasis of tranquility. Start your visit with a stop at John Wesley Church & Nellie Brooks Leatherberry African American Museum located at 4957 Evergreen Road. The cemetery outside this 1875 church building predates the Civil War. The museum hosts rotating exhibits on African American history and culture. Continue on to Oxford and spend an afternoon in Town Park or on the beach area of The Strand. Take time to review Oxford’s 300 year history in the Oxford Museum located in the recreated Federal Customs House at 100 South Morris Street. The collection consists of more than 2,500 artifacts representing the cultural, historic and economic evolution of Oxford from one the country’s earliest colonial ports through the American Revolution, the Civil War, the halcyon days of railroads, oysters and watermen, and its place as one of the premier sailing destinations on the East Coast, 410-226-0191. Be sure to stop by The Scottish Highland Creamery at 314 Tilghman Street for a taste of Award Winning Ice Cream & Sorbets, the most unusual flavor combinations any where! You may also wish to cross the Tred Avon River on the Oxford-Bellevue Ferry. The oldest family-run ferry in the nation, it holds just twelve cars on its 10 minute cruise across the picturesque, peaceful river. After crossing the Tred Avon River, continue on Bellevue Road and stop in at the Gallery By The River offering a look see of the on-going production of hand-woven tapestry, crafted silver and mixed media textiles. Continue on to Royal Oak to Oak Creek Sales, 410-745-3193, a must explore type of “junk to treasurer shop”. The shop is reminiscent of the hunt and peck, with “treasures” everywhere you look.

You can enjoy dinner in Oxford with either fine dinning or casual fare or return to Easton for the evening. Oxford’s Tred Avon Players, 410-226-0061, stage four productions throughout the season and the Oxford Community Center‘s calendar offers a variety of activities. In Easton, restaurants abound from the casual pub to gourmet dining, offering a variety of ambience to suit every taste. Evening entertainment includes the Avalon Theatre, 40 E. Dover Street, 410-822-7299, which offers numerous productions throughout the year. Take in a current run movie at Easton’s Premier Cinema, located in the Tred Avon Square Shopping Center, Marlboro Avenue, 410-822-9950.

Day Two

Start your day at Bishop’s House, or one of the many take away restaurants located throughout Easton. Continue onto St. Michaels (via Route 33), a welcome port on the Miles River. The town is filled with colonial charm and atmosphere. Its main street offers a variety of antique stores and specialty shops that demand to be examined. If you are visiting St. Michaels on a Saturday (May through November), be sure to visit the FRESHFARM Market in Muskrat Park, Green and Willow Streets. Regional growers selling produce and plant offerings including heritage and native species, as well as farm-made products like soap, cheese, and jam. Weekly activities include “Chef at Market” cooking demonstrations and presentations. The FRESHFARM Market is open from 8:30 AM to Noon.

Eating St.Michaels – Friday Afternoon. The Eastern Shore’s premier three hour food tour group. Join us on our adventures inside the restaurants that have impacted St. Michaels’ culinary scene. You will taste food from St. Michaels’ top chefs and learn what inspired them to call this historic town their home. The three hour tour features: a bit and sip at a minimum of four amazing restaurants, behind-the-scenes access to St. Michaels’ food culture; specialty alcoholic or non-alcoholic pairings, a visit to a distinctive culinary shop, and educational and delectable experience. Tours begin at the Chesapeake Bay Maritime Museum. Advanced reservations required. Tickets are $59 per person for all food, beverage, and guidance. E-mail:info@eatingeaston.com or 410-635-4130.

Explore the Chesapeake Bay Maritime Museum, the only museum dedicated to preserving the history and heritage of the entire Bay and its people. Offering nine exhibit buildings and 18 waterfront acres, you’ll learn about the history and the technology that shaped the Chesapeake region. Take in the memorable panoramic view the sailing vessels and pleasure boats in the harbor from the balcony of the 1879 Hooper Straight Light House, located on the grounds of the Maritime Museum.

St. Michaels Museum at St. Mary’s Square, 201 E. Chestnut Street, 410-745-9561, has three 19th century buildings filled with art, artifacts and photographs preserving the legacy of a waterfront town formed in the years after the Revolutionary War. Docent and self guided tours, (maps available at the Museum), are a great way to explore the nooks and crannies of St. Michaels.

After visiting the museums stop by for a taste of wine at St. Michaels Winery, 609 S. Talbot Street, 410-745-0808. Open Monday through Thursday 11 AM – 5 PM; Friday and Saturday 11 AM – 6 PM and Sunday 11 AM – 4 PM. Private tour of the winemaking space by appointment. Not into wine…then stop by the tasting room of one of the original microbreweries on the Eastern Shore of Maryland, Eastern Shore Brewing, located around the corner at 605 S.Talbot Street, St. Michaels. All beers are brewed on the premises, and hand crafted with the finest ingredients. Tours of the brewery are also available upon request. Open Sunday through Thursday Noon to 6 PM; Friday and Saturday Noon – 7 PM. 410-745-8010. Prefer spirits? Lyon Distilling Co., 605 S. Talbot Street, #6, St. Michaels. Tasting and sales of spirits, as well as, tours of the distillery. 443-333-9181.

Celebrate the American love affair with cars by visiting the Classic Motor Museum of St. Michaels, located at 102 E. Marengo Street. Displays of classic cars, motorcycles and other motorized items. Friday, Saturday & Sunday, April through November, admission charge. 410-745-8979

Next stop, a waterside view of Talbot County onboard the Patriot, a 65 foot steel vessel. You will learn the history of the area with a historical narration. The Patriot cruises the Miles River, a beautiful arm of the Chesapeake Bay, on at least three cruises a day. Or, you may wish to enjoy an eco-tour aboard the Princess Royale, which provides an opportunity to meet local watermen and watch their harvesting techniques for the famous Maryland Blue Crabs. If the wind is right, we recommend an afternoon sail or sunset cruise onboard the H. M. Krentz, a 1955 Skipjack, which departs from the Chesapeake Bay Maritime Museum, (boarding passes purchased at the gate), 410-745-6080, or the Selina II, a circa 1926 catboat, 410-726-9400. The Selina II also offers special Moonlight Sailing cruises for romance under the full moon.

Waterside dining available in St. Michaels is perfect for sampling Eastern Shore cuisine and watching the brilliant sunsets over the Miles River. The Crab Claw Restaurant, 410-745-2900, is “the” place for sampling hard shell crabs and The Inn at Perry Cabin’s Sherwood’s Landing, 410-745-2200, offers a unique fine dining experience, or try a local favorite, St. Michaels Crab & Steak House, 410-745-3737, located on Mulberry Street.

Day Three

Continue on a short drive from St. Michaels to Dogwood Harbor on Tilghman Island for sailing onboard the Rebecca S. Ruark, an 1886 Skipjack, 410-829-3976, which is a National Register property. You will cross the busiest drawbridge in the country at Knapps Narrows, servicing the many work and pleasure boats that pass through the Narrows. Jet-Skies/WaveRunners, kayaks, canoes, sailboats, bicycles, power boats, (pontoon, fishing, crabbing, pleasure), motor scooters, & crab/fish gear may be rented at Tilghman Island Marina Rentals, 410-886-2500, for exploring the Island’s shoreline. Tilghman Island is home to some of the best sport fishing charters for rockfish, bluefish, red drum, black drum, trout, croaker & spot on the Chesapeake Bay. Charter boat fishing excursions leave early in the AM and provide a full or half day of activity, Class Act Sportfishing Charters, 410-924-4201, and Diving Ducks Outfitters, 410-886-2528. If discovery of lighthouses are on your agenda, Chesapeake Lights, 410-835-1630, offers three different tours ranging from 3 hours to full day trips aboard M/V Sharps Island, a former U.S. Navy special operations vessel. The Tilghman Watermen’s Museum, 6031 Tilghman Island Road, (Saturday only), explores the unique culture and heritage of Tilghman Island through artifacts and the work of local artists, 410-886-1025.

Waterside dining available on Tilghman Island is perfect for sampling Eastern Shore cuisine and watching the brilliant sunsets over the bay. Marker 5 Restaurant & Tiki Bar, 410-886-1122, located on the 6178 Tilghman Island Road, features waterfront dining, Characters at the Bridge, 5949 Tilghman Island Road, 410-886-1060 with a beautiful but casual spot right on Knapps Narrows in the shadow of the drawbridge. The Tilghman Island Country Store is a small local market offering deli food, take out and general market sundries. Well stocked beer, wine and liquor selection should you wish to grab a bite to go and relax in the park.

Day Four

A diverse inventory of over 600 species of native shrubs, trees, wildflowers, grasses, and ferns is offer by the Adkins Arboretum located in Ridgely, Maryland. Visitors to the Arboretum can choose self-guided walks on four miles of paths through a variety of habitats or docent-guided walks through forested and meadow paths landscaped with native gardens. A Native Plant Nursery is available for purchasing that special landscape item. Special events are also scheduled, phone 410-634-2847 for these activities.

Pickering Creek Audubon Center offers Guided Walks on the 1st & 3rd Sundays of every month, April thru May at 2 PM, June thru August at 9 AM, and September thru November at 2 PM, 410-822-4903. Canoes may also be rented at Pickering Creek with a nominal membership fee.

If rest and relaxation is the center piece of your day, indulge in a therapeutic massage or facial at one of the many spas in the area. Advance reservations are required. The following are just a few located in Easton either a few blocks from Town Center to within one mile: Massage in Motion, 10 S. Hanson Street, Suite 7, 410-310-6649; Time to Feel New Massage Therapy, 111 West Street, 410-770-4447; Serenity Massage Therapy, 33 East Dover Street, 410-770-3573; Massage Plus, 32 South Washington Street, Suite 4, 410-829-9896; Massage Works Associates, 8675 A-5 Brooks Drive, 410-820-4240; Relaxation Station, 8695 Commerce Drive, Suite 1, 410-822-2055; Bodywork by Britni, 29523Canvasback Drive, Suite 101, 410-714-2510 and Foremost Massage & Esthetics, 8706 Commerce Drive, Unit 2, 410-310-7510. We recommend that the reservation be made two weeks in advance of your visit.

Day Five

Explore the countryside on bicycles. Complimentary bicycle use is available for our guests, or bicycles may be rented at various locations; Shore Pedal and Paddle, St. Michaels; orEaston Cycle and Sport, Easton, 410-822-7433, Tilghman Island Marina Rentals, 410-886-2500, throughout the county for half and full day rentals. The local near flat to flat terrain is very popular with first time as well as experienced cyclists. Routes may be chosen ranging from 10 to 60 miles through the scenic and picturesque area. The most frequently traveled bike route is the Tred Avon Circle (35 miles) which provides a full day adventure. The Tred Avon Circle takes you from Easton through the quaint historic town of Oxford, across the Tred Avon River on the Oxford-Bellevue Ferry; through the village of Royal Oak on to St. Michaels, the home of the Chesapeake Bay Maritime Museum and back across Oak Creek to Easton.

Another recommended cycling route is the Cross Island Trail on Kent Island in Queen Anne’s County. The round trip 12 mile trail begins at the Chesapeake Exploration Center, Exit 41 off of Ocean Gateway Highway (Route 50). A trail map published by the Queen Anne’s Department of Parks and Recreation may be obtained at the Center. The bike trail proceeds to the end of Kent Island and returns back to the Center, with most of the trail having a paved surface with a small beach (sand & packed stone) section. Spectacular views of the Chesapeake Bay & the “Bay Bridge”.

Day Six

The Bishop’s House location on the Eastern Shore of Maryland provides visitors with a central point from which to explore the Delmarva Peninsula and other points of interest within a reasonable drive.

Sporting Clays are often referred to as “golf with a gun”. This sport is particularly popular on Maryland’s Eastern Shore for both hunters & non hunters. Whether honing your skills or just having fun, there are several clubs nearby; Del-Mar-VA Sporting Clays, Mardela Springs, 410-742-2023; Woodlands Sporting Clays, Vienna, 410-376-0200 or Pintail Point, Queenstown, 410-827-7065.

Visit the Wye Grist Mill & Museum, (c. 1682), 900 Wye Mills Road, a National Register Landmark, the oldest frame grist mill on the Eastern Shore and the oldest industrial, commercial structure in continuous use in the state of Maryland. The village of Wye Mills, located off Route 50 at Route 662, includes the Wye Oak Park, Wye School, (c.1800), Orrell’s Maryland Beaten Biscuits, the Old Wye Church, (c.1721), and the 19th century United Methodist Church. Wye Mills festivities include a Colonial May Fair & Milling Days during the fall. Grinding Days are on the first & third Saturdays of each month, (May 1st – mid November). 410-827-6909.

Cambridge, Maryland – approximately 30 minutes drive. Located on the banks of the Choptank River, offers a diverse selection of restaurants, marinas, shops, and art galleries. The Cambridge Main Street Farmers Market is open 3 to 6 PM on Thursday, May through October. The red carpet is rolled out every Second Saturday of the month for later shop hours and Art Gallery Walk, featuring refreshments, with live music in many restaurants. Public cruises on the Skipjack Nathan of Dorchester, 410-228-7141, are offered May through October for one and two hour cruises from Long Wharf at the end of High Street, Cambridge’s historic district with cobblestone street. Visit the Choptank River Lighthouse open daily 9 AM – 6 PM May through October, a six-sided screwpile lighthouse, 410-330-8016. Costumed guides lead one hour walking tours every Saturday, (April through October), of the beautiful historic High Street. Reservations for walking tours are recommended 410-901-1000. Be sure to visit RAR Brewinglocated at 504-506 Poplar Street. Craft brews with knowledgeable staff, big screen TV for sports, and even a bag toss game. 410-463-3064. Open daily with extended hours on Saturday.

Vienna, Maryland – approximately 40 minutes drive. Located on the banks of the Nanticoke River in Dorchester County. Vienna was founded in 1706 and has a rich tradition and history. The town prospered through trade and commerce, shipbuilding and nearby tobacco farming. It’s diverse history includes the Nanticoke Indians village, important source of goods and supplies to the Continental Army, supplying Blockade Runners from the south during the Civil War, and its significance as an example of past architecture survival. Take a self-guided tour of historic Vienna. Click to download a PDF file. Be sure to stop into Ewell House, 410-924-3315, a historic waterfront home, built in the 1700’s, which has been repurposed as a Working Art Studio and Gallery. Their offerings include a Working Art Studio, Gallery, Art Lessons, pottery, jewelry, glass and the house has many of the original features of the period. While in Vienna, stop at Layton Chance Vineyard and Winery located at 4225 New Bridge Road, which offers a variety of great wines, 14 acres of beautiful vineyards, a large picnic area with outdoor games, a nature trail, and friendly staff. Listen to music at Happy Hours on Friday nights or bring a picnic and sit outside for Concerts in the Country Series, (check schedule). The tasting room hours begin at 11 AM Monday through Saturday and Noon on Sunday. Vineyard and winery tours are also available, 410-228-1205.

Chestertown, Maryland – approximately 45 minutes drive. Located on the banks of the Chester River, the historic town of Chestertown is the country seat of Kent County. Once a thriving port of entry for colonial settlers, has court records dating back to the 1640’s. Chestertown features many restored 18th century homes, lovely churches, and interesting shops and art galleries. Self-guided walking tours and driving tours of the county are available at the visitors center at 100 North Cross Street. Washington College, the tenth oldest college in the United States, was founded in 1782 in Chestertown. Cassinelli Winery, at 323 High Street, offers their own label wine and spirits for tastings, 410-556-6825. A 3,000 acre wildlife and agricultural area, Chesapeake Farms Wildlife Habitat is located 8 miles east of Chestertown. While visiting Chestertown, stop by and enjoy the sweeping views of the vineyard and the Chester River at Clovelly Vineyards, 301 Clovelly Lane, Chestertown. The vineyard offers wine tasting, events, and tours. 410-708-1775.

Dixon’s Furniture Auction, 2017 Dudley Corners Road, Crumpton, Maryland, 410-928-3006, – approximately 45 minutes drive. Buying & Selling Event held every Wednesday with the inside auction beginning at 8 AM & the outside auction starting at 9 AM. “An Experience You’ll Never Forget”.

Eastern Neck National Wildlife Refuge – approximately 1 hour & 15 min. drive.

Annapolis – State Capitol, Naval Academy, and Harbor, approximately 40 minutes drive.

Baltimore – Inner Harbor, Aquarium, Museums, art galleries, shops, boutiques, unique restaurants all within approximately 1 & 1/2 hours drive.

Chesapeake Wine Trail – Delight in the beauty of the Bay, discover elegance in the bottle. East of the Chesapeake Bay, Maryland’s Eastern Shore is abundant with seafood, beaches, wildlife and history, and now a beautiful and delicious wine trail.

Washington DC – Nation’s Capital, approximately 1 & 1/2 hours drive.

Winterthur Museum & Country Estate – A great American country estate offering a variety of tours, exhibitions, American antiques, and glorious landscaped woodlands and gardens, approximately 2 hour drive.

Longwood Gardens – Premier horticultural display garden, approximately 2 hour drive.

Assateague Island – Consists of three major public areas: Assateague Island National Seashore, Chincoteague National Wildlife Refuge, and Assateague State Park, approximately 2 & 1/2 hours drive.

©2019 Copyright - Bishop's House Bed & Breakfast - All Rights Reserved - Photos may be subject to separate copyright