The quaint town of St. Michaels offers an irresistible dichotomy as soon as you hit its main drag, Talbot Street.
Busiest on weekends during warm months, St. Michaels wears its rich history as a shipbuilding hub on its sleeve, but in recent years, it has also embraced businesses and events that are drawing a younger crowd to the Eastern Shore town, about a 90-minute drive from Baltimore. An array of outdoor activities adds to the appeal, too.
Standing inside one of those operations, Lyon Distilling, the booze brand’s co-owner Jaime Windon said recently she sees more younger visitors walking the town — usually with pet in tow — than she did when she moved there less than three years ago. This charm of old and new has drawn new families to spend weekend getaways, and in some cases, to move there, she said.
“There are more dogs than babies here,” Windon said, “but we’re seeing a lot more babies, too.”
Spending a day there recently, it was clear St. Michaels packs a lot to see and do in a small town (population: around 1,000). For first-timers or those who haven’t been in years, consider this a primer of what not to miss.
Chesapeake Bay Maritime Museum: Since 1965, this museum has celebrated the people and history of the Chesapeake Bay with interactive exhibitions, demonstrations and boat rides. 10 a.m.-4 p.m. through April (and November-March); 9 a.m.-5 p.m. May-October. Free (active military, kids 5 and under and members)-$15. 213 N. Talbot St. cbmm.org.
St. Michaels Museum: Learn about the city’s past through artifacts, oral histories and activities at the museum at St. Mary’s Square. Beginning May 7, the museum will also offer a morning walking tour ($5 ages 7-17, $10 adults) led by a docent. 1-4 p.m. Friday and Sunday; 10 a.m.-4 p.m. Saturday between May-October. $1 (ages 6-17)-$3. Located at corner of East Chestnut Street and St. Mary’s Square. stmichaelsmuseum.org.
Eastern Shore Brewing: Alcohol production has become its own tourism industry, and it didn’t take long for St. Michaels to join the fun. Grab a pint (or a growler) of St. Michaels Ale in the dog-friendly tasting room at the Old Mill, where bands perform from 3-6 p.m. Saturdays. Noon-6 p.m. Sunday-Thursday; noon-8 p.m. Friday-Saturday. 605 S. Talbot St. easternshorebrewing.com.
Lyon Distilling: While everyone hops on the bourbon craze, this distillery — another operation in the Old Mill — produces small-batch rums, corn whiskey (think moonshine) and limited runs of rye whiskey. Try the unaged white rum, which just won a bronze medal from the American Distilling Institute. “A white spirit is often the hardest thing to make and to be done well, because you’re not hiding behind anything,” said Windon. 1 p.m.-5 p.m. Monday-Friday; noon-6 p.m. Saturday (with distiller-led tours on Saturdays, 2 p.m. and 4 p.m.). 605 S. Talbot St., No. 6. lyondistilling.com.
Come by Chance: Owner Debbie Jackson describes her shop as a “very relaxed, coastal lifestyle” store. The home decor items reflect the vacation-on-the-water vibe of St. Michaels. (We really liked the gold anchor bottle opener ($18).) The store’s casual but sharply designed layout is the result of a dedicated staff, she said. “It takes a village to keep the store looking like it does, and everybody is so proud to work there,” Jackson said. 10 a.m.-5 p.m. Monday-Thursday; 10 a.m.-6 p.m. Friday-Saturday; 11 a.m.-5 p.m. Sunday. 202 S. Talbot St. 410-745-5745.
Olivins: For the foodie constantly searching for new specialty items, Olivins sells infused olive oils, balsamic vinegars, coffee, locally made chocolate and other pantry-enhancers. 10 a.m.-4 p.m. Monday, Thursday-Friday; 10 a.m.-5 p.m. Saturday; noon-4 p.m. Sunday; closed Tuesday-Wednesday. 205 N. Talbot St. olivinsstmichaels.com.
Ophiuroidea: Known locally as “The O,” this shop has local art, salvaged furniture, pet gifts and other unique items. 11 a.m.-5 p.m. Thursday; 11 a.m.-6 p.m. Friday-Saturday; 11 a.m.-4 p.m. Sunday; closed Monday-Wednesday. 609 S. Talbot St. ophiuroidea.com.
Silver Linings: This sterling silver and gemstone jewelry shop has eye-catching, regional-specific items like the Chesapeake Summer Necklace, whose pendant is a blue crab next to an Old Bay box ($150). 10 a.m.-5 p.m. Monday-Saturday; 11 a.m.-4 p.m. Sunday. 203 S. Talbot St. silverliningsmd.com.
Chesapeake Trading Co.: Another lifestyle store, this attractive shop has furniture, clothing and house-decor accessories. And if you forgot something for your weekend getaway — say a book, DVD or CD — Chesapeake Trading Co. has a selection of those, too. 10 a.m.-6 p.m. Monday-Saturday; 10 a.m.-5 p.m. Sunday. 102 S. Talbot St. 410-745-9797.
Eats and drinks
Ava’s: Since opening in 2008, this pizzeria and wine bar has established itself as one of the town’s most popular eateries, thanks in large part to the pies coming straight from its oak-fired oven. 11:30 a.m.-9:30 p.m. daily. 409 S. Talbot St. avaspizzeria.com.
The Crab Claw: Owners Bill and Sylvia Jones opened this St. Michaels landmark in 1965, and it’s been serving residents and visitors alike a menu filled with seafood dishes. They are particularly known for their crabcakes ($27.95 for two). Free dockage for boats, too. 11 a.m.-9 p.m. daily (through November). 304 Burns St. thecrabclaw.com.
Foxy’s Harbor Grille: With weekly live music, a wide-ranging menu and a rotating selection of 15 draft beers, this restaurant offers both a fun atmosphere and a comfortable spot to eat leisurely. Noon-9 p.m. daily (kitchen closes then but bar will stay open later for customers) through October. 125 Mulberry St. foxysharborgrille.com.
Town Dock Restaurant: On the same property as Foxy’s, Town Dock allows patrons to enjoy lunch or dinner — usually seafood, but also steaks and pastas — outside with a waterfront view. There’s also a room with a view of the water for private parties of up to 60 people. 11:30 a.m.-9 p.m. (last seating) Thursday-Monday; closed Tuesday-Wednesday. 125 Mulberry St. towndockrestaurant.com.
208 Talbot: Windon said this quiet restaurant has some of the best food in town, so we found out for ourselves. The shrimp and cheddar-jalapeno grits ($19) were wonderfully rich, while the crab spring rolls ($12) made the jumbo lump protein the rightful star of the show. We spent dinner at the bar, chatting Orioles with the friendly bartender. 5 p.m.-8:30 p.m. Thursday-Friday; 5 p.m.-9 p.m Saturday-Sunday until beginning of May. From May until it closes in the fall for the season: 5 p.m.-10 p.m. Wednesday-Sunday. Closed Monday-Tuesday. 208 N. Talbot St. 208talbot.com.
Chesapeake Skipjack Sailing Tours: Take a ride on the historic, 27-ton skipjack H.M. Krentz. Captain Ed Farley leads the tours, which he says aim to relax customers but also educate them on the bay’s ecosystem. The No. 1 question he gets? “They all want to know if they’ll get seasick and the answer is no, because the boat is so steady,” Farley said. From mid-May to Oct. 1 with three trips offered daily (11 a.m.-1 p.m.; 2-4 p.m.; 6-8 p.m.). Check oystercatcher.com for prices once the season opens.
FreshFarm Farmers’ Market: Purchase cheese, meats, fruits, vegetables, flowers and more at this weekly market. 8:30 a.m.-11:30 a.m. Saturdays through mid-October at the municipal parking lot behind 208 S. Talbot St. freshfarmmarkets.org.
Motor Museum Saturday Cars and Coffee: There are worse ways to spend a Saturday morning with a cup of coffee in hand while checking out vintage rides. If you have one in your garage, bring it. 9-11 a.m. Saturdays through Nov. 5. 102 E. Marengo St. stmichaelsmd.org.
Activity rentals: From paddleboards and kayaks to bicycles and electric bikes, this rental shop will get you moving, either on the water or through the St. Michaels streets. If you really like what you rent, there are options to buy, too. Bikes start at $10/hour; kayaks and paddleboards begin at $20/hour. 500 S. Talbot St. shorepedalandpaddle.com.
Bay Day: This free event at Tilghman’s Philips Wharf Environmental Center (less than a 20 minute drive away) has scientists and experts teaching kids everything about the Chesapeake Bay, from oyster restoration to storm water management. 11 a.m.-3 p.m. May 14. pwec.org.
St. Michaels Ghost Walk: Legend has it St. Michaels is prone to visits from ghosts. Find out for yourself on this 90-minute walking tour. The first of the season is 7:30 p.m.-9:30 p.m. Saturday. $9 (kids ages 8-12)-$15 (adult). Starts at the Maritime Museum (213 N. Talbot St.). chesapeakeghostwalks.com.
Patriot Cruises tour: Since 1969, Patriot Cruises has offered rides down the Miles River aboard the Patriot, a two-level, 149-passenger cruise boat. $5 (kids ages 3-11)-$24.50. 12:30 p.m. and 2:30 p.m. Saturdays and Sundays through mid-May. Summer schedule (mid-May-mid-October): 12:30 p.m. and 2:30 p.m. Monday-Friday; 11 a.m., 12:30 p.m., 2:30 p.m. and 4 p.m. Saturday-Sunday. Departs from Maritime Museum (213 N. Talbot St.). patriotcruises.com.
Model skipjack races: Organized by the Maritime Museum’s Model Sailing Club, these races (occurring on select Sundays through mid-October) feature radio-controlled skipjacks speeding through the water. The public is encouraged to watch from the museum’s Fogg’s Cove waterfront. Season opens May 15 (11 a.m.-2 p.m.). Free. cbmm.org.
WineFest: The 7th annual gathering of wine enthusiasts will feature hundreds of wines from around the world (including Maryland), many of which will be discounted. The night before (April 22, 6 p.m. and 7:30 p.m.), there will be VIP tastings of extremely rare and reserve wines unavailable to the rest of the festival. $50-200. Various locations throughout the town. Noon-5 p.m. April 23-24. winefestatstmichaels.com.
St. Michaels Running Festival: Now in its fifth year, this festival offers a 1K Kids Fun Run for children 12 and under, a 5K run/walk and a half marathon. $25-$110. Race begins at St. Michaels High School (307 Seymour Ave. ), with on-site registration kicking off at 5:30 a.m. May 21. runstm.com.
St. Michaels Brewfest: Happening across three locations (Eastern Shore Brewing, Foxy’s/Town Dock and the Crab Claw), this celebration of beer boasts more than 70 craft beers from local, regional and national breweries. $44. Noon-5 p.m. June 4. stmicaheslbrewfest.com.
St. Michaels Concours d’Elegance: On Sept. 25, the 10th annual event will celebrate vintages cars and luxurious fashion. Schedule of events and prices to be announced. Tickets go on sale June 1. Takes place at Fogg’s Cove at Maritime Museum (213 N. Talbot St.) Visit smcde.org for updates.
Snuggery Bed and Breakfast: This bed-and-breakfast claims to be St. Michaels’ oldest residence, but don’t worry — it’s been modernized. Choose from the romantic Waverly Suite or the more low-key Harbour Room. Rates range from $200 to $250. 203 Cherry St. snuggery1665.com.
Point Breeze Bed and Breakfast: This three-room B&B has a 150-foot dock overlooking the water for fishing, crabbing or simple relaxing. Breakfast is served on the screen porch. Rates begin at $205. 704 Riverview Terrace. pointbreezebandb.com.
The Harbour Inn: With 17 rooms and 32 suites, the Harbour Inn has plenty of space, but it’s the amenities that make it stand out: Free bicycle rentals, an outdoor pool and complimentary resort shuttle service that will take you all around town. 101 N. Harbor Road. Go to harbourinn.com for rates.