Kent County MD: Chestertown, Betterton, Rock Hall

WHY GO: You won’t believe who washed ashore and stayed in Kent County MD on the Upper Chesapeake Bay. The towns of Chestertown, Betterton, and Rock Hall indeed embrace a group of quirky and exceptional personalities. And a getaway here will introduce you to each and every one.

There was a retired Ivy League college professor who opened a shabby chic Music Hall with 125 seats, and enticed jazz great, Charlie Byrd, to play. (McHugh sadly passed away in 2021).

Downtown Chestertown MD

There’s a brilliant antique appliance restorer who left the Defense Department after 35 years to follow his passion, a furniture maker who has made it his life’s work to help others create their own heirlooms, and much more quirk in an achingly beautiful region where everyone seems to have a back-story.

Craft a bench, take a sunset cruise, swim in a clean, nettle-free beach, listen to some new World Music, and stay in a luxury bayside inn or retreat on this Tidewater Getaway.

Kent County is on our list of 17 Best Romantic Getaways in Maryland. Check it out for more adventures with your loved one.

Things to Do in Kent County MD

Chester River Packet Chestertown Kent County MD
Chester River Packet Chestertown MD

TOUR/BOAT: Chester River Packet

Sailing up and down the Chester River at sunset is one of life’s great pleasures. Especially, if done on a 1920’s style wooden yacht with a drink in hand. The Sunset Dinner Cruise offers a modest ham and salads dinner buffet (with cash bar), for just $35 pp.

Sunset via Chester River Packet Chestertown MD
Sunset via Chester River Packet Chestertown MD

But the star of cruise is the riverscape and the spectacle of shadow, light, and color as the sun goes down. This mellow excursion seems to attract a bevy of girl/guyfriend groups, romantics, and anyone who revels in the communal celebration of days end. $35pp adults, $20 kids  for 2-hour tour includes casual buffet style dinner. 

Robert Ortiz Furniture Maker Chestertown MD
Robert Ortiz Furniture Maker Chestertown MD

MAKE OR BUY/FURNITURE: Robert Ortiz, Furniture Maker, Chestertown

Robert Ortiz has been fashioning Shaker and Japanese style furniture in this studio for 22 years and came to a stunning revelation when he helped a client make a piece for his home. The man returned twice more in order to build the same thing three times. Turned out, this customer had three sons who all coveted the same console table he’d made with Ortiz’s help.

Woodworking wtih Bob Ortiz Chestertown Kent County MD
Woodworking wtih Bob Ortiz Chestertown MD

Studies have shown that Millennials don’t want their parent’s “stuff.” However, they will accept an heirloom made by Mom or Dad, especially if said heirloom is a striking wooden bench or table.

So, Ortiz decided to open his furniture workshop to the public for 5 day workshops – one on one – where he guides crafters through the process of wood selection from the mill, and then through design, joinery, and finish, using the same tools, jigs and fixtures he’s developed over the years.

At the end of five days, you take home an heirloom-worthy piece of furniture. This is not, says Ortiz, a “Master Class.” The daily sessions are project oriented and an experience. “You’ll walk away with furniture you’ll treasure the rest of your life.” 5-Day Workshops from $2450 – $3750 depending on piece made. Does not include housing. 

This was chosen as one of the Best Places in Maryland to Pop the Question

Dave Hoatson Owner Chestertown Electric MD
Dave Hoatson Owner Chestertown Electric MD

SHOP: Chestertown Electric, Chestertown

Dave Hoatson, an electrical engineer in the defense industry for 35 years, wished to retire to a small riverfront college town and concentrate on his passion: repairing small antique appliances. But he didn’t know if his repair shop would be a store or museum.

Turns out, it’s both. In Hoatson’s tiny storefront a few blocks from the Chester River, you’ll find some strikingly beautiful, museum-quality phones, fans, lamps, clocks, and other early 20th century electrical appliances from before the 1930’s, in various stages of repair.

Phones Chestertown Electric MD
Phones Chestertown Electric MD

Surprisingly, “You can call your Mom” on a 1913 Candlestick Phone, which would have cost $2.20 when new. The 6’4” soft-spoken Hoatson “loves” his work, and has stories about every piece in his shop.

Fans at Chestertown Electric MD
Fans at Chestertown Electric MD

Of all the devices, the two most eye-catching are a 1914 General Electric ($900) and a 1934 Emerson Silver Swan ($300). Both were designed by a woman – interior designer Jane Evans – who told the President of Emerson Electric that his fans were ugly.

So he challenged her to design a beautiful one. She did. Both are fully functional and throw out more breeze than most fans of their size today. Fan fans come here from all over the country (yes, there is a Fan Club). So, if you’re in town, drop in to say hi to Dave and pick up that dial kitchen phone from you nostalgic dreams.

Book Plate Bookstore exterior in Chesterfield MD

SHOP: Bookplate Bookstore, Chestertown

Some of the top authors today come to The Bookplate – a humble, friendly, and knowledgeably staffed mostly-used-books bookstore – to speak. Lately, Evan Osnos (Wildland: The Making of America’s Fury), was scheduled for end of April ’22.

Welcome Home Gift and Home Goods shop in Chestertown MD

SHOP: Welcome Home Gift Shop, Chestertown

Say you’ve maxed out of space for kitchen tools and house-ware doodads in your home. No problem. Shopkeepers at the adorable, and well-stocked Welcome Home will steer you to the coolest, and most of-the-moment things you didn’t know you needed: and that don’t take up much room (e.g. long thin spatula for deep jars).

Front of Mainstay Rock Hall MD
Front of Mainstay Rock Hall MD

MUSIC HALL: The Mainstay, Rock Hall

*Sadly, The Mainstay founder, Tom McHugh, passed away in 2021. But his vision rocks on.

Nearly three decades ago, college PhD Professor and jazz trumpet player, Tom McHugh, walked into this storefront space and saw potential. Despite being told it would never fly, McHugh opened up The Mainstay as concert hall for all kinds of music. With a concentration on jazz.

The Mainstay Rock Hall MD
The Mainstay Rock Hall MD

McHugh set up couches and chairs in front of a little stage. He ran the Mainstay, modestly, for a year before calling Charlie Byrd in Annapolis through a number he got from a phonebook.

“You’ve Got Charlie Byrd”

Figuring he was calling Byrd’s management office, McHugh was surprised to find the jazzman himself on the line.

McHugh told Byrd he could offer him $300. “Is that for each of my band or total?” asked Byrd. “Total.” “Let me see what the guys say,” Byrd said. He called back minutes later with a “yes.” “We all got our start in places like yours,” he added, by way of explanation.

McHugh recounted that Byrd told him he had a friend “from NY” who wanted to jam with him. So it came to pass that Charlie Byrd and John “Bucky” Pizarelli headlined at this rather boho music hall in a tiny Maryland town.

Tom McHugh Founder The Mainstay Rock Hall MD
Tom McHugh Founder The Mainstay Rock Hall MD

Currently, Charlie Byrd’s widow runs the Mainstay Bar. To date, over a thousand concerts have been held here, from the Preservation Hall Band to Femina (who counts among her greatest fans the rocker Iggy Pop).

Carol Colgate is now the Director of the concert venue, which has become an economic driver for the town. Patrons come from DC, Philly, and Baltimore, to hear everything from Blue Grass to World, Folk, Funk, Indigenous, Hip Hop, and of course Jazz, in an intimate space.

You’ll still find the original hodgepodge of couches and chairs that can seat 125, “135 if you cram them in.”  On any given night, the “savvy and attuned” spectators love to speak to the musicians after the show. Said McHugh, “The room, audience, musicians, and music, together create a weird synchronicity that is magic.”

TOUR/SAIL: Blue Crab Chesapeake Charters, Rock Hall

Captain Mark Einstein, and his first mate/wife, Suzanne, run 1 ½ hour day sails and sunset cruises from the marina next to Waterman’s Crab House. $35 pp for 90 minute cruise.

Downtown Rock Hall MD
Downtown Rock Hall MD

WALK: Rock Hall, Kent County MD

Rock Hall is a home base for watermen, and known for its 13 marinas and harbor. As a “boaty town,” in fact, many yachtsmen know Rock Hall only from the water, especially if they tie up to the docks to dine at the classic Waterman’s Crab House and then leave.

Stay longer, though, to explore downtown a block over. Take in a concert at The Mainstay (see above). Stop in Smiling Jakes for Island Wear. Check out Hickory Stick for “Eastern Shore Gifts for Home and You.” Stop at Get the Scoop for a cone or cup of ice cream.

Java Rock - Rock Hall MD
Java Rock – Rock Hall MD

COFFEE/SHOP: Java Rock Coffee House

Leave a bit of time to rest at Java Rock Coffee House – not your humdrum Starbucks. This coffee shop also sells wine, gifts, and irreverent (some would say naughty) novelties. A “community hub,” locals come every day and order brews like Brown-Eye Girl (mocha with extra espresso shot), Night Owl (mucho caffeine), and Mocha Mint Patty, among other lattes and espresso drinks.

Pirates and Wenches Weekend Rock Hall MD
Pirates and Wenches Weekend Rock Hall MD

It’s here that many a plan is hatched for community events – like the now annual Pirates and Wenches Weekend, with a completely made-up back story of Greybeard the Pirate’s ties to Rock Hall. Everyone gets involved, with decorations and “y’arrrr sales.” The event draws between 5,000-8,000 people to this town of 1,300.

HIKE: Eastern Neck National Wildlife Refuge

Wildlife viewing is virtually guaranteed at this 2,285-acre island refuge, a major feeding and resting spot for migrating and wintering waterfowl. There are 6 miles of trails and roads including a handicap-accessible boardwalk. Open all year, 7:30am- 30 minutes after sunset. Closed to general public during certain hunting seasons. 

Betterton Heritage Museum MD
Betterton Heritage Museum MD

GO: Betterton Museum at the Town Office, and Betterton Beach, Betterton

Before the Bay Bridge was built in 1952, and before Ocean City MD became all that, steamer boats and ferries brought thousands of people per day to Betterton Beach.

In Betterton’s heyday, there were 17 hotels, dance halls and bowling alleys. Now, with a year round population of just 300, (doubling in the summer), the pristine beach is quiet and peaceful.

Learn local history –  from John Smith on – in this small museum in an old converted Catholic Church. The former Church of Most Precious Blood now serves as Betterton’s Town Office and Community Center.

John Smith’s notes about this waterfront paradise enticed settlers, who planted tobacco, peaches, and tomatoes. The area was also found to have “good fishing.”

Heyday of Betterton Beach

So, by the late 1800’s, Betterton MD was attracting an ever growing number of people who’d fish, swim, stay in one of the 17 bare-bones hotels. (With no indoor plumbing, guests swam in the freshwater rivers to clean off). Visitors would then return, rested, to Baltimore.

Betterton Beach MD
Betterton Beach MD

The Baybell Steamboat carried 2,500 people at a time, 80,000 people per weekend, to swinging Betterton Beach known for “Boating, Bathing, Bowling, and Dancing.”

After the Bay Bridge opened, the Atlantic Ocean beaches became more popular. Subsequently, Betterton and greater Kent County MD, became a quiet bedroom community with “second homes.”

But lately, people are rediscovering this little jewel, with it’s good, clean, crisp water, no sea nettles (a problem elsewhere), a fine sandy beach without “towel to towel” crowds, a public bath house, grills, and a pavilion you can rent on a bluff overlooking everything. Museum open Sat/Sun April-Oct. 1-3, Beach 24/7.

GO: American Legion, Betterton

According to a local, “The American Legion is now the hot spot in Bettertown, particularly when local musicians and singers (an the occasional comedian) show up to jam and entertain the crowd in the lounge on the Thursday Open Mic Nights. An inexpensive meal special is offered each week.”

Best Restaurants in Kent County MD

Watershed Alley entrance Chestertown MD

EAT: Watershed Alley, Chestertown

In 2022, Chef Rodney Scruggs left The Occidental Restaurant in Washington DC to open the charming, cool, and extremely hot-at-the-moment Watershed Alley in this little Eastern Shore burg. In Chestertown MD, Rodney and his pastry-chef wife, Lisa, are the proverbial big fish in a small pond, culinarily speaking.

Contemporary art on walls of Watershed Alley Chestertown

But that seems to be changing, even by gracious Rodney’s admission. The Retriever, Watershed’s next-door neighbor, owned by Neyah White, is “also quite stunning.” Neyah’s wife, Brandywine, owns Stam’s, an ice-cream/lunch spot down the street. Seems that little Chestertown is just getting started.

Full interior view of Watershed Alley MD

For now, though, Watershed is Chestertown’s destination restaurant. Their “Contemporary American” – American classics “with a twist” – is drawing patrons from DC, Baltimore, Philly, and even more farther flung.

Open kitchen and modern staircase Watershed Alley Chestertown MD

Décor is of this place, 100%. Scruggs was sure to find local artisans and craftsmen (within 100 miles) to create a one of a kind artsy, modern, creative ambiance. Chesapeake-area folks donated driftwood for a prominent wall sculpture.

Driftwood art at Watershed Alley Chestertown

Scruggs tapped artist Marci Dunn Ramsey to adorn the walls of the chic dining room. Woodworker, Vicco Von Voss, crafted the tables and the exquisite open brass, wood, and glass staircase leading to the second floor.

Oyster shell chandeliers at Watershed Alley restaurant Chestertown

Upstairs, in the banquet “Estuary Room,” chandeliers made from strands of dangling oyster shells set the mood. The second floor also sports two more rooms – the private 12-person Perch Room (“perched” over a balcony overlooking the first floor and kitted out with paintings of Perch fish), and the quiet Pub Room.

Bad Alfreds Distillery Chestertown MD

TASTE/DISTILLED: Bad Alfred’s Distilling aka BAD, Chestertown

The only distillery in Kent County MD – all brandy, gin, and bourbon made here is “grape based.” That’s because owner, Alfred Cassinelli, has a winery as well, and uses his own Grappa and Lemoncello in his recipes.

If the hard stuff is too hard for you, Bad Alfred’s got something good for sweet-tooth’s. “Girl Shine” Apple Brandy is the counterpoint to its Moonshine. Come in for a taste, and stay for a bite – you’ll find “from scratch” pub food that includes Cassinelli’s own Red Sauce concoctions. And wood fired pizza!

EAT/CHESTERTOWN: Locals also love

The above-mentioned Retriever for cocktails, oysters, and small bites. Casa Carmen – a winery tasting room and tapas place owned by two Ecuadorian polo players. The Imperial for hand-cut fries. Stam’s for lunch and ice cream.

Eastern Shore Food Lab Chestertown MD

Eastern Shore Food Lab (offering classes) and its own Modern Stone Age Kitchen, which specializes in sourdough breads and crusts (come for Friday Night Pizza). The Chester Riverfront 98 Cannon has not yet recovered from a fire, with no plans to reopen anytime soon. Uncle Charlie’s Bistro, known of its Bourbon Bacon Ice-Cream.

Where to Stay in Kent County MD

Blazing fire adds romance to a manor inn library Chestertown MD

STAY: Great Oak Manor, Chestertown

We deem this luxury inn, right on the Chesapeake Bay, with its own private beach, a Maven Favorite. Read our complete write up of Great Oak Manor in this post. 

Guest Room Inn at Haven Harbour Rock Hall MD
Guest Room Inn at Haven Harbour Rock Hall MD

STAY: Inn at Haven Harbor

This chic 9-room inn is part of a yacht marina complex that includes two pools, shuffleboard, Fishing Pier, Restaurant and Bar, and a huge Marina store.

Chairs behind Inn at Haven Harbour Rock Hall MD
Chairs behind Inn at Haven Harbour Rock Hall MD

But the Inn itself sits about a block away from the Marina. Though on a main road it backs up to a cove where guests can just grab a kayak or SUP from the dock and go forth into the water. No paperwork involved.

Kayak Dock Inn at Haven Harbour Rock Hall MD
Kayak Dock Inn at Haven Harbour Rock Hall MD

The Inn is run more like a Guest House than a hotel. (In this case with no innkeeper on premises, you get your key from the Marina office).

Rooms are nevertheless upscale, bright, nautical, and spacious. Some sport balconies overlooking the Inn’s dock and marina beyond. Décor is Chesapeake-chic – heavy on anchors, ships wheels, oars, crabs, sailing ships, and sea charts.

Great Room Inn at Haven Harbour Rock Hall MD
Great Room Inn at Haven Harbour Rock Hall MD

There are several small common rooms on the first floor. But the Great Room is where it’s happening. The game and huge TV room is stocked with snacks and drinks throughout the day. Every morning from 7:30 to 10, this is where you’ll find a hot Continental Breakfast.

Breakfast Inn at Haven Harbour Rock Hall MD
Breakfast Inn at Haven Harbour Rock Hall MD

Room rates from $125, Balcony Deluxe Rooms from $185 per night include hot Continental Breakfast, use of bikes, kayaks, pool, snacks.

Guest Room Inn at Huntingfield Rock Hall Kent County MD
Guest Room Inn at Huntingfield Rock Hall MD

STAY: Inn @ Huntingfield Creek, Rock Hall

Owned by Jim and Joanne Rich (who also own Java Rock and other in-town businesses) the Inn at Huntingfield Creek is one of the top places to stay in Rock Hall. It consists of 7 cottages and 5 rooms in the main house – all with Temperpedic Beds – on 70 acres.  Over 40 of this acreage are soybean, Sunflower, and lavender fields.

Wedding Venue- Inn @ Huntingfield Creek - Rock Hall MD
Wedding Venue- Inn @ Huntingfield Creek – Rock Hall MD

As befits a Select Registry property, guest quarters are exquisite, and the grounds as a whole are quite popular for weddings. There’s an open-air barn dressed up for events, and an arbor outside for nuptials. With a saltwater pool, organic garden, and kayaks to use on Huntingfield Creek – that feeds into the Chesapeake Bay – this is on many a Chesapeake Region Stay List. Rooms from $175-$325 per night. Cottages from $265-$345 per night.

Kent County MD Getaway Pin

Kent County MD Pin


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine,, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

6 thoughts on “Kent County MD: Chestertown, Betterton, Rock Hall”

  1. Wow ! Beautiful post man! second time reading your post ! I can’t not like a short space for a TV room.
    Thanks a lot for sharing this awesome post with us!
    Love your blog!

  2. Updates: Tom McHugh, founder of the Mainstay, passed away in 2021. The Mainstay carries on. Barbara’s on the Bay is a victim of the pandemic and Barbara was forced to close permanently in Dec 2021. The American Legion is now the hot spot in Bettertown, particularly when local musicians and singers (an the occasional comedian) show up to jam and entertain the crowd in the lounge on the Thursday Open Mic Nights. An inexpensive meal special is offered each week.

  3. Hi Michael – Thanks so much for the updates. I will correct the post to reflect this – and letting me know about the American Legion. That’s a bit of small town info I love to pass on! Malerie

  4. Update: Durding’s store is no longer operational. For great ice cream (pets and humans), Get the Scoop (referenced in your article) is located in the quaint village shops. Fresh Start Food and Garden is a great place to snag a scrumptious deli sandwich or locally grown produce or meats.

  5. It’s a shame Wendy Culp wasn’t mentioned as the owner of the Watershed restaurant. She also assembled all the art on display. She, and her husband Larry, also own the buildings that house the Retriever and Stam’s. Wendy is responsible for the renovations in all three buildings. The Culp’s have been a great addition to Chestertown, and deserve more than a little credit.
    I know the article can’t credit everyone, but there were many locals involved, such as Joe Karlick and Rob Glebe. Even non-locals, such as Kathryn McGowan, Wendy’s right hand person.

  6. Hi John – thanks for reading and commenting. Yes, I wish I could give credit where credit is due with all enterprises I cover, but as your comment shows, once you start, the list gets too long for a blog post attempting to describe worthy places to go in one whole MD county!! Thankfully, comments like yours fill in some blanks! – Malerie

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