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The Mainstay

5.0 (3 reviews)
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The Retriever Bar and Oysters - The House Burger

The Retriever Bar and Oysters

4.3(40 reviews)
10.3 mi

Picked the Retriever for dinner out with friends during my bachelorette weekend and so glad we did…read more Apps and cocktails were on point (strawberry Negroni!) and our server Tessa was so sweet. Love that they serve local oysters.

The Retriever Oyster House in Chestertown left us with a mixed impression, one that deserves a fair…read moreand constructive take. We had just come from a college football game and, on the fly, decided to grab dinner here based on the recommendation of the one local in our group. There were seven of us, and most went for the double smash burgers with fries, which were excellent. Kim, our server, was outstanding, prompt, accurate, and attentive throughout the evening. The bartender also added to the positive side of the experience, making sure everything at the table ran smoothly. The issue came at the door. We had tried to call ahead to let them know we were on the way, not realizing that OpenTable was their preferred system. When we arrived, the host made this clear, but in a way that was unnecessarily sharp and cold. It set the wrong tone for the night. In a town where friendliness is the norm, the contrast was striking. The experience began under a haze that was difficult to shake, even though the food and drinks were excellent once we sat down. To be constructive, this is less about policy and more about hospitality. A host sets the tone, and a welcoming explanation could have changed everything. Something as simple as, "We usually use OpenTable to handle groups this size, but I'm glad you're here, let's get you taken care of," would have gone a long way. Instead of frustration, it could have created a positive first impression and likely earned a loyal group of returning guests for years to come. Inside, the atmosphere was lively, with locals enjoying themselves in a loud and fun environment. Our group of longtime friends who have been convening in Chestertown for two decades fit right in once we were seated. However, the bad first impression lingered, and as a result we only had one round with food before deciding to leave a lot earlier than our normal rhythm for an evening out. We ended up taking our bar bill to another venue. Great food and excellent table service carried the night, but the host made sure we will not be returning as part of our annual tradition. This is a restaurant with strong potential, and it could go from good to exceptional with just a little more attention to how guests are greeted.

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The Retriever Bar and Oysters - The bar

The bar

The Retriever Bar and Oysters - Apple strudel

Apple strudel

The Retriever Bar and Oysters - Shrimp & Grits

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Shrimp & Grits

Carpenter Street Saloon

Carpenter Street Saloon

3.8(147 reviews)
24.3 mi
•$$

After spending the afternoon wandering through the shops in St. Michaels on my first-ever visit to…read moretown, I found myself craving one thing for dinner. A really good burger. Actually...a really good burger with crab dip on it. Naturally, I started searching for somewhere that could satisfy both cravings at once and landed on Carpenter Street Saloon, a laid-back local watering hole that's been serving up food, drinks and good times in the heart of St. Michaels for decades. Their menu had both burgers and crab dip, but not together. Challenge accepted! I arrived around 4:30pm on a Friday during Fourth of July weekend and somehow managed to snag the very last parking spot in their small lot. Even better, as I walked inside, a booth just inside the front door opened up. The adventure gods were clearly looking out for me! The atmosphere was exactly what I was hoping for. Folks were gathered around the bar enjoying drinks, conversations filled the room and absolutely nobody cared that I had wandered in by myself for dinner. Sometimes that's exactly the kind of place you need after a long day of adventuring. I studied the menu for approximately three seconds before asking my waitress what I assumed would be a ridiculous question. "Could I get a burger...with crab dip on it?" Without missing a beat, she smiled and said, "Absolutely! We actually used to have that on the menu, but nobody ordered it." I couldn't stop grinning! "Well," I replied, "I'm somebody...and I want it for dinner tonight!" One more vacation victory! For $16.00, my custom Bay Burger arrived piled high with rich, creamy crab dip and melted cheese dripping over the thick burger patty exactly as I'd imagined it. It was everything I'd hoped it would be! Juicy burger. Creamy crab dip. Gooey cheese. The combination just...worked! In fact...it worked so well that I briefly considered ordering another one before remembering I still had dessert plans later that evening. (Responsible Adult Alexis eventually won that internal debate.) I chose the coleslaw as my side, and while the flavor was really good, it was a little drier than I personally prefer. That's entirely a preference thing, though. If you're someone who likes a less creamy coleslaw, this one will probably be right up your alley. My Diet Pepsi was $4.00, bringing my total to just $21.20 before tip. Honestly, for a custom burger loaded with crab dip in the middle of one of Maryland's busiest holiday weekends, I thought that was an excellent value. Carpenter Street Saloon isn't trying to be fancy. It's comfortable. It's welcoming. It's the kind of neighborhood bar where locals and visitors alike can settle in, enjoy a great meal and relax for a while. If you're visiting St. Michaels and find yourself craving a burger, do yourself a favor...ask them to bring back the crab dip burger. Apparently nobody orders it. Except me. And now hopefully you!

Oh man!! Where to start! Walked in with my sister to a VERY lively group that was singing along…read moreto somebody playing guitar music. Our server(s) - Phoebe and Sophia - came to us immediately to offer water, etc. They answered questions about cocktails and differences between food items that helped us decide more easily. We ordered wings (old bay garlic honey sriracha - delicious), onion rings, the foot long glizzy (it was fried and had a perfect snap) with tater tots and crab balls (OMG, so fresh, you could taste the freshness) for dine in, and we took mozzarella sticks and crab dip and our leftovers to go. We also joined the "party" haha - I had a watermelon crush and my sister had a blackberry lemonade something or either. The service was great, it was a party vibe going on on a Saturday, and they had convenient parking behind the restaurant. Good value for the price and I would ABSOLUTELY go back!

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Carpenter Street Saloon - Atmosphere

Atmosphere

Carpenter Street Saloon - Rockfish fish and Chips

Rockfish fish and Chips

Carpenter Street Saloon

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Freeman Arts Pavilion

Freeman Arts Pavilion

3.9(31 reviews)
76.2 mi
•$$$

Last year I rated this venue the top 5 Stars. Having been recently renovated I would now rate this…read morevenue even higher. Having visited this venue multiple times in the past, we always thoroughly enjoyed attending concerts on the original stage. The Joshua M. Freeman Foundation was established in 2007 with a clear mission: to enrich the Delmarva region through the transformative power of the arts. Founded to honor the enduring legacy of Josh Freeman--a dedicated business leader and philanthropist who believed deeply in community--the organization was built upon the fundamental principle that the arts should be accessible to everyone. This vision became a reality in the summer of 2008 with the debut of The Freeman Stage at Bayside, which originally featured a modest, covered wooden stage set on a small grassy patch within the Bayside community. What began as a simple summer performance series rapidly blossomed into a cherished community gathering spot, welcoming local families, national touring acts, school groups, and thousands of enthusiastic arts lovers each season. Driven by a phased expansion strategy and a capital campaign, the Freeman Arts Pavilion is transitioning into a premier outdoor performance venue capable of hosting around 4,000 guests, equipped with state-of-the-art production technology and enhanced comforts for both performers and attendees. We attended the grand opening of this new stage on July 8th to catch the Matteo Bocelli World Tour. Arriving around 5:45 PM, we found the main lot completely full and had to park in the secondary lot to the right of the entrance. After waiting in line for about 20 minutes, we entered using our QR-coded tickets. We walked up the boardwalk to our seats in section 303, row P, seats 17 and 18. The total cost for our two tickets including Allianz Global Assistance insurance was $375. I am not sure how much the insurance cost was, but days before the concert we could have purchased similar row P seats for under $100 per seat without any insurance. Next time we will not purchase insurance. The new stadium seating is a massive upgrade over the previous flat lawn setup with folding chairs; these seats are permanently set in concrete and offer plenty of space to stretch out and unwind. For our next visit, we intend to secure seats closer to the main stage in sections 202 or 102. Matteo treated the crowd to an encore, which we stayed to enjoy, before making our exit during his final number. By taking the alternative route via Sound Church Road out to Route 54, we successfully bypassed the typical post-event traffic. Refer to my many videos and pics from our event. I will return here with my friends for a George Thorogood And The Destroyers concert so more to come from me.

My wife and I have attended several concerts at this venue over the past several years with my…read morebrother-in-law and sister-in-law. Most recently (Oct. 2026) we had the opportunity to see Styx. The pavilion underwent a complete renovation in 2025 adding more seats, a larger stage and more food vendors. It seats approximately 4500 people including the lawn area. All of the seating is outside with no roofing. I found it strange that with the renovations covered seating would not have been added. Every seat offers an excellent view of the stage, due to the seating being arranged like a stadium. Acoustics are very good with plenty of speakers allowing the music to be heard throughout. There are approximately six food trucks and several concession stands offering Mexican food. seafood, burgers, fries, etc. Alcoholic and non-alcoholic beverages including beer are also offered. Food prices average about $20/person. Parking is free and plentiful and well organized by the venue staff (all volunteers). There a couple of regular bathrooms as well as Port-a-Potties. More bathrooms would be useful and helpful. Lines are common during events. The crowds are well behaved and security consists of volunteer staff members and Delaware State Troopers. I appreciate that the pavilion helps support the music arts and our youth. This is a beautiful venue in a beautiful area. I recommend this location for a nice, relaxing evening out with friends and family.

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Freeman Arts Pavilion
Freeman Arts Pavilion
Freeman Arts Pavilion - Grounds

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Grounds

Phantom Power - NEIPA in the beer garden.

Phantom Power

4.8(4 reviews)
59.8 mi

Be the first to review this somewhat hidden gem of a music venue and brewery? don't mind if I do!…read more Over my past couple of years of listening to them, Foxy Shazam has evolved into being a band that I really needed to see live. So when I saw that they were playing this random Millersville venue not all that far away I was instantly intrigued, and then I was even more sold when I saw that the venue also brewed their own beer. I also loved that it was a non-Ticket Master venue that used Eventbrite to sell tickets without an insane amount of hidden fees. And when I checked it out it was a hidden gem of a pleasant surprise. Unless you go to Millersville University, the area that the venue is at is one that you might not frequent. But Phantom Power is one of those few other reasons to visit since it delivers a fine assortment of local flavor events and national touring acts. Regular events include things like gothic/industrial dance parties, comedy nights, a Kegs and Eggs weekend brunch event, or just chilling in their outdoor beer garden on good weather days. I would absolutely go to things like these if Millersville was even closer! But on the flip side Phantom Power has also been seeing a good surge of national acts coming through thanks to WXPN taking notice for shows and them just being a fun and reliable space which I'll get to. In addition to Foxy Shazam I've seen big local names like Hop Along and mewithoutyou, indie acts like Delta Spirit and Sondre Lerche, Industrial and Punk bands like Front 242 and Reverend Horton Heat, and WTF WoW shows like Tim Cappello from Lost Boys (I still believe! - https://youtu.be/LpuwcINDHnQ) on their current and past lineup. It kind of reminds me of pleasantly filled memory venues of yesteryear like the Trocadero, only with a better beer list! Once we made our way through the lot to the venue we realized how big it is. Outside of their brunch event, they don't have a menu of their own, but I love the food truck connections they have and really wish I could remember the name of the BBQ truck that had those glorious smoked wings! The on-site brewed beer was as much of a hidden gem as the music venue since we enjoyed IPAs, stouts, pilsners, ESBs, and some other good varieties. The one suggestion I have is that, with a music venue of its caliber that also has a good beer list, it would be useful for them to have more sheld space to leave cups on during a jam-packed show like the one we were at, Foxy Shazam is one of those good energy rock bands that I would have enjoyed without good sound or lighting. But the fact that they had both in spades definitely helped. Now that I know this hidden gem is a success I'm checking their Facebook and Eventbrite pages (they don't actually seem to have their own site outside of those) for eye-catching shows, and you should do the same!

The venue this place has to offer is some that I would not normally attend.( so I thought) i I been…read moretrying out new things. Staff here was down to earth and pleasant. The place was laid off nicely with two levels. The have a bar on both levels. Very small bar food menu. This is not a restaurant. Snack type hot food only. The entertainment tonight I was surprised. They were actually very good. And when I read what they had on their calendar they had some stuff that interest me. Yes this place is geared towards a younger demographic. At least compared to my age..I recommend you check out the web site. They have a lot to offer.I was there for about three hours. I prepaid for my ticket. . It end up being a very inexpensive night of entertainment.

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Phantom Power - Har Mar Superstar on opening night.

Har Mar Superstar on opening night.

Phantom Power
Phantom Power

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Red Eye's Dock Bar - Crab pretZel dip

Red Eye's Dock Bar

2.8(81 reviews)
11.4 mi
•$$

Making our way by motorboat to Red Eye's via Chestertown, we were looking for some cold beer and…read moresnacks after an hour boat ride. How lucky we pulled up at 2:45 and were able to dock for free. Lucky because we were told there would be a $10 cover after 3 PM. For 6 of us that was going to be pricey. We were able to get a patio table by the water and had exceptional service by Catherine. The shrimp tacos and margaritas were delicious, as was the crab dip and nachos. Intrigued by the cover charge and enormous presence of roided security guards in tight t-shirts, we asked what in the world was going on. Well, it just happened to be their busiest day of the year: The Bikini Contest Finals, starting at 5:00 PM. Sadly for us (especially the guys), we would have to depart for our long boat ride back to Chestertown, meaning we were going to miss the bikini contest. They were not kidding about it being the biggest event of the year! As we were leaving the area, there were tons of motorboats lined up to enter the marina. Wow! What a fun day, on the water in excellent weather, with great service and friendly customers. A cool vibe was evident.

This was the most disappointing crabcake ive ever had from a resteraunt in Maryland. There was more…read morebreadcrumbs than meat, no seasoning to even try to make it taste like a crabcake. Sent it back, the next was just as bad. How can you charge $27 for breadcrumbs??? It was disgusting. Pretty bad when $16 coldcuts are so much better than a $27 breadcake.

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Red Eye's Dock Bar - Red Eyes Dock Bar

Red Eyes Dock Bar

Red Eye's Dock Bar - Patio area

Patio area

Red Eye's Dock Bar

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The Mainstay - musicvenues - Updated October 2026

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