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    The Freeze

    4.0 (38 reviews)
    Open • 11:00 am - 9:00 pm

    The Freeze Photos

    THE FREEZE ATMOSPHERE

    What's the vibe?
    Quiet
    Divey
    Good for groups
    Dogs allowed

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    Frozen logo and such.
    Josh G.

    Feeling hot? Then The Freeze is for you. Well, it's for you if you enjoy ice cream and fast food and a feeling almost like some kind of small town spot from the 1950's or something out of a tv show about middle America. "Hey, wanna go down to The Freeze?" Sure, let's head on over! This Chestertown staple holds no place to actually sit as it's more of an indoor counter area where you'll order up and then eat outside (or in your car). You can't miss the place driving by. Between the giant frozen lettered logo and a life size replica of Mater from "Cars", you'll know you've found it. I've been here twice and both times it was for the same thing: a milkshake. Let's just say the second trip was due to the first. My girlfriend and I were here for round 1 a year ago in June and then again earlier this month. We entered post-dinner time and wanted dessert, choosing one of their many milkshake flavors. Peanut butter was the winner for us both and it did the trick with a vanilla base and plenty of what seemed to taste like Reese's as the PB. Don't like peanut butter? (Who are you!?) There's plenty of other options with more than fifteen milkshakes to choose from. Beyond that, you'll find a menu of fried food favorites and ice cream with tons of toppings, because it is called The Freeze, right? Right. Overall, The Freeze kinda feels like a place frozen in time from its old school looks and classic setup. It's no destination spot, but if you do find yourself in Chestertown on a hot summer day, get cool in here.

    Swirled waffle cone

    Visited from DE. Saw this nearby and wanted to try it out. My friend got a grilled cheese and that took little too long for them to make but i got ice cream and it was soooo good! Very old timey feel inside too! Something straight out of a movie lol.

    the sign on the roof of the store
    Hannah H.

    The Freeze, which was once known as Downey's, is an old-school diner-esque carry-out place, serving up burgers, subs, ice cream, sundaes, and milkshakes. The hubs and I came here while we were in the area, and we ordered the following: an Oreo milkshake (this was not too thick and not too thin, had a good amount of Oreo within, and made with softserve; it was pretty good), a Butterscotch milkshake (I was not a fan of this, as it had no butterscotch taste to it; the vanilla soft serve also seemed to have been tainted with the butterscotch syrup that was supposedly used), and The Big Freeze (this was a Big Mac-esque type of a burger; a sesame seed bun filled with two juicy patties and all of the works, including Thousand Island dressing; this was really delicious! Since it was hot off the griddle, it was super hot and juicy; all of the condiments inside also made this burger pretty good - the relish, the ketchup, the mustard, the cheese, the onions, etc. It gets a little sloppy, but it's worth it!). Just note that there are a couple of benches to wait for your order to be ready, but it's strictly a carry-out place. The staff here are no-nonsense, but friendly. There's a $10 minimum, and plenty of parking in their private lot. +The Big Freeze! :D +Oreo milkshake +carry-out only +free parking

    11/03/11

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    4 months ago

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    3 years ago

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    3 years ago

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    2 years ago

    Great service awesome ice cream and huge portions!!! I got a milkshake & loved every second of it

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    2 years ago

    Wonderful local place. Old school ice cream, cold beverage, and food. Friendly and helpful. Patient with the "newbie"

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    3 years ago

    Average icecream basic two flavors. Not much to talk about. Staff is polite and friendly.

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    9 years ago

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    4 years ago

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    3 years ago

    Retro place with all your favorites! Twist cones, banana splits, milkshakes and burgers!! Check out how clean the flat top is!

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    4 years ago

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    10 years ago

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    3 years ago

    Amazing food and friendly service! I would recommend this place to anyone new in the area!

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    6 years ago

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    15 years ago

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    6 years ago

    Love it. Best soft serve ever. So creamy and the hot fudge is perfect. They give you huge portions too.

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    4 years ago

    There is no place to sit inside or out. The staff seemed inexperienced. The ice cream was nothing special.

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    5 years ago

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    7 years ago

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    6 years ago

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    7 years ago

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    5 years ago

    Cute little place but No table & chairs to sit & eat, not even outside. And WHERES MATER??????????

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    8 years ago

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    9 years ago

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    5 years ago

    Always friendly and the best fries, burgers, and shakes! Their Ice cream cones are always a treat!

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    10 years ago

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    8 years ago

    Big freeze is the ultimate burger. Service isn't fast and not dine in but everything is fresh

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    9 years ago

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    12 years ago

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    13 years ago

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    9 years ago

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    9 years ago

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    10 years ago

    Stopped in for a wedding and got three milkshakes. They were three of the best milkshakes I've ever consumed. They are to die for.

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    10 years ago

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    11 years ago

    Love grabbing subs here, or a quick sweet treat. Chicken philly is great. Legit milkshakes

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    11 years ago

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    8 years ago

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    13 years ago

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    Ask the Community - The Freeze

    Review Highlights - The Freeze

    “We got a delicious sundae with hot fudge and a waffle cone with soft serve.”

    Mentioned in 2 reviews

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    The Retriever Bar and Oysters - The House Burger

    The Retriever Bar and Oysters

    4.3(40 reviews)
    1.1 mi

    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.

    This was a fun place. We came visiting friends while in town for the Tea Party weekend, so they get…read morea little pass for being busy. I'm not sure the menu was all that imaginative, but the food was good and we enjoyed some oysters, onion dip, and I had the chicken sandwich. Our waiter was very attentive. The only thing I may add is to think about better flexibility on seating. It's a very large bar but the sit down area isn't greatly configurable. We'd put in for a group of 6 but it was not possible for them to seat us all at one table.

    Photos
    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

    Bad Alfred's Distilling - Cross Street and Cannon Street Pizzas

    Bad Alfred's Distilling

    4.2(46 reviews)
    1.1 mi

    To be honest, it was a full bladder that got us in this place. How fortunate for the rest of us…read morethat someone had to go! While waiting, the rest of us decided to get some pizzas to go and have a beer. We sat at the back bar area and enjoyed a Tooshie Mango Hazy IPA and chatted with our server, Jennifer. Our pizzas and side salad were ready in no time, and we were on our way. I regret not taking a photo of the side salad. It was so colorful and fresh - I gobbled it immediately. Having not had salad in a while due to the cyclospora outbreak, this salad offered euphoria. Organic mixed greens, shaved parm, shredded carrots and cherry tomatoes made a plentiful and healthy side to the amazing pizzas I was about to dive into. The Cross Street Pizza came with a thin and crispy crust, pepperonis and mozzarella with a red sauce. DLicious! The Cannon Street Pizza was abundant in sweet Italian sausauge, mushrooms, cheese and red sauce. Yummers! Nice ambiance here - sort of dark and cozy with a bar type feel, great pizzas, excellent salad and tasty beer!

    So frustrating. You go into this place and you're invisible. Been here a few times, food is very…read moregood, but their process stinks. My wife and I waited to be seated, no hostess showed up. We sat at their bar and were invisible. One waitress said " she'll be right over". Don't know who she was as no one came over. Terrible service! We went down street to Retriever and had a great dinner

    Photos
    Bad Alfred's Distilling
    Bad Alfred's Distilling - Two pizzas on menu

    Two pizzas on menu

    Bad Alfred's Distilling - Tooshie Mango Hazy IPA

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    Tooshie Mango Hazy IPA

    Arby's

    Arby's

    2.1(7 reviews)
    0.1 mi
    •$

    I came to Arby's wanting to try their food for the first time. I come in and this teenage girl…read morecomes in from the side door and asks if I need something. I tell her I want to order something and she laughs and says something like "okay then why don't you tell me what you want?" Really awkward. As I tell her my order, she looks like she's having a bad day which makes me feel more uncomfortable. My food comes out a few minutes later and the food was a 3/10. I got the cheese pit beef sandwich and fries. I couldn't taste the cheese on the sandwich and the fries were decent. Overall, i probably won't come here again. If you're an Arby's fan, be aware of this kind of service

    Being a Sunday night, and nothing else in Chestertown open, i was surprised it was pretty clean,…read moreorder filled quick and the food well prepared. Portions seemed a bit small, the Pecan chicken sandwich had a small plop in the middle, not visible around the edges of the bread, not at all like the picture on the poster Sauce dispensers were out of the pepper sauce. My slider buns were soft however, so that was good ! Staff was super pleasant, and no pushback when I asked for extra Horsey Sauce packs. I noticed the drive through clock was averaging 240 seconds , which is not bad for an Arby's . I almost rang the "great service" bell, but figured they probably are tired of hearing it. I just thanked them the old fashioned way , verbally and sincerely .

    Photos
    Arby's
    Arby's
    Arby's

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    The Freeze - hotdogs - Updated October 2026

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