Inn at Perry Cabin

Experience luxury and elegance at one of America's most prestigious resorts. Dine with royalty-worthy views of Chesapeake Bay – enjoyed by none other than those in Wedding Crashers! Sip tea amidst the waterside restaurant or cozy up by a roaring fireplace as you savor classic pub fare. Spectacular scenery is guaranteed!

Crab Claw

Perhaps the Chesapeake’s most legendary crab shack steeped in local traditions and offering some of the best seafood this side of the Eastern Shore. Outdoor tables overlook Miles River to provide an unrivalled dining experience - perfect for those who seek out unforgettable moments with friends or family while indulging on everything from soft shell crabs to oysters. One of the most fun dining experiences you can have!

Patriot Cruises

Experience the beauty and historical charm of our region from a unique perspective by taking one of Patriot's narrated cruises. Spend 65-70 minutes leisurely gliding upriver aboard this cozy craft, sipping on refreshments as you take in the sites from your choice between indoor air conditioned spaces or an outdoor upper deck with plenty of fresh air! Passengers also enjoy complimentary parking, access to bathrooms onboard and special offerings at their classic old bar.

Chesapeake Bay Maritime Museum

Step back in time and explore the historical past of an iconic Chesapeake Bay with a visit to the Maritime Museum on their beautiful property. Founded in 1965, this interactive museum located by the historic town of St Michaels houses artifacts, exhibitions & vessels that give us insight into how Navy Point evolved from seafood packing house docks to today's admired maritime icon. A trip here is a fun activity and sure to be rewarding for any history buff or curious tourist looking for something offbeat!

Sail Selina II

Experience an exclusive getaway aboard Selina II, a luxury sailing yacht. Step onto gleaming mahogany and freshly-polished brass as you set out on a 2-hour journey complete with captivating stories of maritime history - all delivered by 1st class captains and friendly crew. Whether it’s your first ever coastal sail or another day spent amongst natural beauty afloat, step onto Sail Selina II for a unique outdoor adventure!

Foxy’s Harbor Grille

Come and experience the convivial downtown scene like a local! Gather with friends on this vibrant riverfront patio, sipping craft beers on tap while enjoying classic seafood dishes. Enjoy live music as you soak up the ambiance of locals mingling in an energetic atmosphere or on the expansive outdoor patio.

Justine’s Ice Cream Parlour

For over 25 years, this charming ice cream parlor has been enchanting sweet tooths with its creative shakes and sundaes. Step back in time for an old-fashioned ice cream experience in the heart of St. Michael's!

Simpatico LLC

Italy is renowned for its exquisite range of wines, cheeses and delicacies. Simpatico discovers the finest products from Italy's hidden artisan corners to bring excellent products - wine, pastas, sauces - you won’t find anywhere else!

Carpenter Street Saloon

Step inside St. Michaels' beloved Carpenter Street Saloon and you can feel the locals taking a load off since it first opened its doors many years ago. ‘C-Street', as they call it, is open year round Monday & Tuesday at 3:00p.m., and Wednesday to Sunday serving up breakfast, lunch and dinner starting 8:00a.m. With live entertainment most nights including trivia and karaoke, plus pool tables available upstairs for some nightlife fun - there's always a reason to come by Carpenter’s!

Eat Sprout

If you're looking for a meal that nourishes both body and soul, then look no further than this cozy space in St. Michael's! It has everything from organic breads to healthy spreads perfect for snacking - or if it’s just an energy boost you’re needing, grab one of the delightful smoothies or coffees on offer. And enjoy them at one of their outdoor tables as you take in all the energy of St. Michael’s on a sunny day.

Limoncello

Come to this delightful bistro for a truly authentic Italian experience. From creamy risotto and classic pizzas, to an extensive selection of fine wines and spirits - you won't leave disappointed! The menu is a perfect balance of high quality cuisine at an affordable price.

Blue Crab

From cozy corners to read the paper, or a friendly spot for refuge on a sweltering summer day - the Blue Crab coffee shop offers an ideal atmosphere. Their selection of tasty breakfasts lunches, and signature specialty coffees makes it a perfect place not just to relax but even to get some work done!

The Galley

Come to this casual spot for the very best burger in town. They also offer a bottomless mimosas on Sunday. And don't forget about those signature breakfast items! The outdoor patio is ideal for a leisurely lunch or brunch where you can watch life pass by as you sit back with your meal.

Bistro

Bistro is one of St. Michaels' premier destinations for upscale dining. From the cozy atmosphere in a historic setting to their open kitchen's Chef’s Counter where you can watch their culinary team at work - this is a truly elevated dining experience. Bistro’s seasonally-inspired and classically prepared dishes will leave you happy you came.

Ava’s Pizzeria

This quaint spot was once an old historical home known for Jimmy Jump's goose picking service - but now it brings locals something much more delicious: insanely good pizza and meatballs. Pull up a seat outside at their retractable-roofed patio no matter the weather. And beyond their appetizing meals, they also offer plenty of beers on tap! An excellent choice for a casual lunch or a social meal with friends!

Theo’s

Theo’s serves up an inviting atmosphere of easy-going luxury. Savor hand-carved steaks and local seafood while you enjoy craft cocktails or all American classics with a side of southern charm - shorts & boat shoes welcome!

Village Shoppe

A one-stop-shop for all your culinary needs! The Village Shoppe boasts an array of unique meat, cheese, wines and craft beers selections curated by their experienced butcher Adam himself! From ribeyes to sausages, there's no shortage for your next feast with friends. And if on-the-go grub is more up your alley, be sure to stop by they deli section where you can get made to order sandwiches and other delightful items perfect for lunchtime munching!

Lyon Rum

Rum enthusiasts rejoice! Here you can find one of the finest distilleries around. Established in 2012, Lyon Rum tribute to their traditional roots by offering a signature line of rum that's sure to impress you! Come for a tasting, and you’ll be sure to leave with a bottle or few!

Winery

This local maker of 18 wine styles welcomes tastings in its quaint, year-round tasting room. Leave with a local souvenir from their retail shop!

Classic Motor Museum

Get up close and personal with classics from before, during, and after WWII - muscle cars of yore that have been immaculately preserved over time; vintage trucks whose workmanlike craftsmanship will give you an appreciation for all things mechanical; plus motorcycles and other era inspired collectibles! A great activity in the heart of historic St. Michael’s.

Gina’s Cafe

Spice up those hot summer nights with homemade sangria or cool off with a crisp margarita - served alongside nachos of course. A local Tex-Mex favorite that is sure to deliver a great meal and a fun time, their backyard patio is the perfect place to rest your feet and satisfy your cravings!

Bradley Park

Nestled along the quiet, historical streets of St. Michael's lies a vibrant park perfect for families. And their playground is guaranteed to put a smile on your kids' faces!

Rise Up Coffee

Let Rise Up offer the perfect wake-up call for your morning routine. This local coffee company's drive-in stand will deliver bold java that'll have you upbeat all day long - no matter if you're coming or going in St Michaels! Conveniently located in the parking lot of Graul’s supermarket just outside of town.

Graul’s Market

St. Michael’s favorite supermarket! You’ll find everything you need to stock your fridge and pantry, plus a salad bar, deli, and extensive alcohol selection.

Town & Country Wine Liquor Etc

Your solution to all your beer, wine, and spirits needs. One of the most expansive collections around midshore!

Pemberton Pharmacy

Pharmacy and gift shop in the center of St. Michael’s.

Spa at Perry Cabin

At the Spa at Perry Cabin, let your body and spirit rejuvenate with therapeutic massages blended with fragrant plant-based treatments. The spa features handpicked herbs from their own garden and regional farms across Eastern Shore. Take some time away to recharge!

Perry Cabin Park

A simple park just outside of town, featuring a great playground, a basketball court and plenty of green space!

St. Michael’s Marina

Dock your boat in style and leisure. St. Michaels' marina accommodates boats ranging from 25' up to 220', all just steps away from downtown! They provide 10-feet of depth along with diesel fueling services right at your slip - perfect for when you're ready to set sail again.

Gluten Free Bakery Girl

St. Michael's favorite gluten-free bakery! Their full-service, dedicated and certified celiac, gluten-free bakery store leaves a smile on all their customers' faces.

Shore Pedal & Paddle

Kayaks, bikes and stand up paddleboards all available from one awesome rental outfit!

Chesapeake Trading Co

Chesapeake Trading Company is an absolute must for lovers of finer things or anyone who likes a good gift for a friend (or themselves)! From excellent coffee tables and reads to fine women's apparel and artisan jewelry and stylish hats; not to mention Dash & Albert rugs that will bring some coastal color into your home decor. But this haven isn't just about fashion - Chesapeake also has a wide selection of books & music to please anybody stopping in!

Country Comfort Farm

Featuring a variety of farm animals, fresh produce, and homemade treats, as well as a welcoming and friendly atmosphere that makes visitors feel right at home.