Checkers Family Restaurant

Restaurant
9516 Windsor Blvd, Windsor, VA 23487, United States +1 757-242-3136
(189 Reviews)

Description

Checkers Family Restaurant is situated at 9516 Windsor Blvd, Windsor, VA 23487, United States. This restaurant type venue has received 189 user reviews and has a total menu that includes popular items such as Homemade Chicken Salad Sandwich, Mushroom Swiss Burger, and Swiss Bacon. It's known for family-style dining with a variety of classic American dishes.

Categories

Restaurant

Amenities

  • Takeout
  • Dine-in
  • Delivery
  • Great dessert
  • Serves local specialty
  • Solo dining
  • Wheelchair accessible entrance
  • Wheelchair accessible parking lot
  • Wheelchair accessible restroom
  • Wheelchair accessible seating
  • Coffee
  • Comfort food
  • Dessert
  • Table service
  • Restroom
  • Cozy
  • Accepts reservations
  • Credit cards
  • Debit cards
  • NFC mobile payments
  • Good for kids
  • High chairs
  • Kids' menu
  • Free parking lot
  • Free street parking
  • Parking

Checkers Family Restaurant Photos

Reviews (189)

4 Superb Reviews Out of 189 Reviews
Amazing
128
Great
33
Okay
14
Not Great
3
Terrible
11
  • Jennifer
    Mar 07, 2026 - 12:35 am

    I hadn't been there in years. I just randomly stopped, and as always, they didn't disappoint. The service was great, I wasn't feeling well, and they really took the time to answer questions while I made up my mind and quickly got it out to me so I could get home. I got the poppers, the Philly, and sweet potato fries. All were delicious and made exactly how I asked for it to be. I will definitely be going back and taking the kids.

  • Alton Ashworth
    Feb 14, 2026 - 5:10 am

    After many years of passing this place, Paw researched it and reviews said there where known for there burgers, so we stopped. Friendly staff. Jennifer brought us to rolls to get started while we looked at the menu. All your favs apps, salads,burgers,sandwiches,steaks and seafood. Both of our burgers were hand patted fresh and delish okra was good fries also. So if your driving down 460 stop in as say hi to Jennifer and get your grub on.

  • Sherry Ellis Freeman
    Feb 07, 2026 - 4:20 am

    Small, family restaurant that serves down home food. Comfort food. It sits on busy rt 460 in Windsor, VA. Serving breakfast, lunch & dinner. They have specials. I had the hamburger steak w/onion & mushroom gravy. Mashed potatoes & gravy. Served hot & fresh. Service was quick & friendly. Dining area was clean & quaint in decor(local artists paintings). Prices are very reasonable & menu is not overwhelming. Plenty of free parking. If ur looking for down home cooking this place has you covered!

  • Karen Smith
    Feb 01, 2026 - 10:56 am

    I was driving through Windsor and was hungry, so I decided to try something different than a chain restaurant. I happened upon Checkers and stopped there. I was greeted and was able to choose where I wanted to sit and I chose a window seat. There were so many selections on the menu that I liked. I decided on fried shrimp which came with two sides. I chose a loaded, baked potato, sweet potato fries, and green beans. Yeah, I paid to have an extra side cuz I wanted it! Everything was yummy! I also liked the paintings on the wall and these little miniature creations of little houses/rooms that lit up. I will definitely be coming back again soon. :)

  • The Erica
    Jan 03, 2026 - 6:39 am

    The food was unbelievable! I am so surprised at how a little place has such a great selection on the menu and such excellent service and quality food! This is our new go-to spot! Brandy was a wonderful waitress! Thank you for the great experience! We will be back ASAP!

  • Holly Brock
    Dec 21, 2025 - 2:54 pm

    My daughter-in-law said this place has been around for many, many years. And we were super surprised, the food was fantastic. I got pork chops, and I felt like fred flintstone with a bronto burger.

  • alli g
    Dec 18, 2025 - 7:47 pm

    I was overall happy with my order everything was really good the steak could have been seasoned and cooked a little bit better but for this area it was a decent meal. I was happy that they had blue cheese dressing that the salad was fresh I was also happy that they had lemon for my tea. It is really close to Blackwater Birds and Bees Farm.

  • Daisy May
    Dec 03, 2025 - 3:19 am

    PRESENTATION WAS UGLY This place is a hidden gem. Their hours are Tuesday through Friday, 11am-8pm. They are closed Saturday, Sunday, and Monday. We Googled " Food near Me" while traveling through Windsor, VA. and this restaurant came up. I read the reviews. Although I read both positive and negative reviews, we decided to have our own experiences. I ordered the bake potato and chili. I know the presentation could use more effort, and the outer skin of the baked potato should be better, but it was okay. My husband ordered the hamburger steak with gravy. Both dishes were really delicious. We enjoyed our experience here, and we said we would be back again. By the way, the prices were so reasonable and that's why I give it 5 stars.

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