Such a cute place. The girls taking care of us were very helpful giving us samples. I had coconut…read moreand it was delicious with actual coconut pieces. We really loved the ice cream. We have gone to another location but this was our first time here.

In the summer, I never say no to ice cream. Sugar Doodles Sweet Shops features both Hersey ice…read morecream and Vanderwendes ice cream (a personal favorite). While the workers weren't very attentive, the store was clean and open with lots of seating. The coconut ice cream with chocolate sauce was delicious. Street parking was available right outside. While my family and I tasted a lot of samples, you can never go wrong with chocolate or vanilla. Some honorable ice cream flavor mentions that aren't pictured are apple pie, blackberry, and cookie dough. The small is a very generous scoop and leaves you feeling satisfied. The prices are fair, especially for a small town. We appreciate an ice cream store that is open every day, as it is always nice to support a business every day of the week.

More menus! They have a large variety of milkshakes too, the Snickers Bar was my favorite!read more

Fun spot found on the main street going through Chestertown that has solid eats. Can't miss their…read moresign. It's an independent burger joint/ice cream shop, and I love to support spots like these. Had a good burger with wonderful, crispy onion rings and a huge, tasty vanilla shake. All made in front of me. It's a throwback place with reliable cooking, quick service, and personable staff. Keep it up, Freeze. I'll be back.

For the last few months I've been curious about a cookie dough milkshake, Everytime I've gone to a…read moredifferent ice cream store (including the other Sugar Doodles) they've given me cookies and cream. Today I had my first Cookie Dough Milkshake, absolutely incredible.

This shop has a great selection of ice cream and toppings. The coconut with fresh pineapple on top…read morehit the spot. Service was very fast and the price was decent. I'd recommend this if your in the area

Some of the best icream east of the Chesapeake Bay!…read more If you're looking for a sweet treat Sugar Doodles is worth a stop. There's 3 locs that I know of and this location has outdoor and indoor seating and plenty of parking.

Lots of options. Lots of sweets...ice cream,…read moreDoughnuts, cake pops, cookies stuffed with ice cream, smith island cake, dirty soda and more. Which you may not know is they have a small breakfast menu, and crepes for anytime of the day. Good service. Indoor and outdoor seating, And a nice location.

I was confused when I arrived because all the reviews mentioned homemade ice cream, but it had a…read moreHershey's ice cream ad out front. Upon entering, the young woman showed us 2 cases of Hershey's ice cream, and one of fresh homemade ice cream, just made in-house. She also showed me another freezer chest with pints and quarts of other homemade flavors. I was definitely all about the homemade stuff. Got two scoops, Oreo and Peach! I had checked their social media to see posts about the fresh peaches they just got for the ice cream, it was really good! They post regularly, so check that out for their latest flavors! Loved the Oreo too... that was my toddler's favorite. Huge portions! I could not finish it all. My toddler liked the pictures on the walls, especially the posters of a kitten and a giraffe eating ice cream. Cheesy but adorable touch! The young woman who helped us was so kind and sweet... explained all the flavors and said we could sample if we weren't sure. She was in the middle of talking to us when some male employee appeared, took over in an authoritarian way, with no discussion with the woman, and just gave our total, like "where's the money" all brusque and pushy. That young woman was personable and deserves 10 stars; the guy was obnoxious. I wanted to tip the young woman but they don't let you do it with c-card, and I had no cash. So bring cash for tips! I didn't see Mommom... is she fictional or real? Or a spirit watching over us? Any which way, I'm happy I stopped, and will definitely visit again! Tip-- if you want lunch or dinner, stop at the Little Grocer nextdoor. They too have great reviews!

I can't speak too much on the atmosphere as my eyes went straight to the ice cream when I walked…read morein. I was able to try some of their unique flavors. I settled on two scoops (absolutely huge scoops) a scoop of coffee Oreo and a scoop of monster (the blue at the top). I'm an ice cream lover and this did not disappoint. Can't wait to get more this summer.

Best coffee chocolate chip ice cream, ever!!! The service is amazing, too. A joyful place.read more

The ice cream was really good! The staff is very friendly and attentive, and they have a cool…read morelittle spot right off of rt50 with plenty of space to hang out in the shade.

This cute ice cream shop has a great variety of ice cream and toppings, and the prices are great!…read moreWe visited the shop twice during our stay in Rock Hall. The young ladies working there were very sweet.

[Coronavirus review] This is one of a set of a half-dozen or…read moreso wooden shacks that appear to form the "downtown" of Rock Hall. They have an ordering window and a pickup window, and you can order while maintaining a reasonable distance. For some reason, they've renamed their mint chip and mint oreo flavors into something less intuitive, forcing me to ask and have them tell me that it was just mint chip and mint oreo. I ordered the latter, plus a scoop of black cherry. You might be skeptical of combining mint and cherry, but it actually works really well (as I've learned from getting the occasional cherry on top of mint milkshakes). The cherry had whole cherry pieces, and the price for two scoops was low, so I was satisfied. The mint was nothing special. They do have some flavored ice for someone wanting non-dairy refreshments. Presently, the bench next to this place is taped over, but it's not far to the bayside anyway and there's a small beach, so I say drive over while that ice cream's still cold.

Love, love, love the Nottingham Inn! Breakfast is delicious, lunch is pretty yummy too! Waitstaff…read moreis great! The Creamery has a nice variety and the staff is always friendly!

We stopped in on the way home for a quick lunch since we were passing through. Super cute and tasty…read morefood! Service was too notch too! We plan to stop in again when back in the area!

Delicious crepes & coffee on the water along the Cross Island Trail. Perfect stop off spot when…read moreheading out on your boat or bike.

The warmed walnut maple scone was yummy--and scones are not typically a favorite of mine. The…read moredouble espresso was rich hot and bitter (in the right way).

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.