Cheddar Jackson
522 N 2nd St, Richmond
(804) 225-8882
Customers' Favorites
Tomato Basil Soup Brooklyn Grill Cheese
Alt Alice Swiss & Gouda Vo
Brooklyn Grilled Cheese
Vegan Grilled Cheese
Smoked Robinson
Gourmet Cookies
Bottle of Water
Sugar Cookie V
Tomato Soup
Panini
Featured items
Oozlefinch - Boozy Orange Soda - 7.5%25 ABV - 16oz Can
Gluten-Free Hard Orange Soda - 7.5% ABV
Bryant's Cider - Unicorn Fuel - 6.9%25 ABV - 16oz Can
Dry Cider with Rose Hips and Hibiscus.
Oozlefinch - Boozy Cream Soda - 7.5%25 ABV - 16oz Can
Gluten-Free Hard Cream Soda - 7.5% ABV
Archer Roose - Bubbly Rosé - 11%25 ABV - 250mL Can
Fragrant and seductive, with aromas of rose, white fruits, and wild strawberry.
Archer Roose - Bubbly Cuveé - 10.5%25 ABV - 250mL Can
Crisp and dry. Fruit-forward notes of pear and apple. White flowers on the nose.
WINE & MIMOSAS (Available To-Go)
Archer Roose - Bubbly Cuveé - 10.5%25 ABV - 250mL Can
Crisp and dry. Fruit-forward notes of pear and apple. White flowers on the nose.
Archer Roose - Bubbly Rosé - 11%25 ABV - 250mL Can
Fragrant and seductive, with aromas of rose, white fruits, and wild strawberry.
BiggAzz Mimosa
16oz Mimosa with Bubbly Cuvée, and your choice of juice or nectar.
LOCAL BEER (Available To-Go)
Oozlefinch - Boozy Grape Soda - 7.5%25 ABV - 16oz Can
Gluten-Free Hard Grape Soda - 7.5% ABV
Oozlefinch - Boozy Orange Soda - 7.5%25 ABV - 16oz Can
Gluten-Free Hard Orange Soda - 7.5% ABV
Oozlefinch - Boozy Cream Soda - 7.5%25 ABV - 16oz Can
Gluten-Free Hard Cream Soda - 7.5% ABV
Bryant's Cider - Brite Good Dry Cider - 6.9%25 ABV - 16oz Can
Dry Cider. 100% Sugar Free
Bryant's Cider - Unicorn Fuel - 6.9%25 ABV - 16oz Can
Dry Cider with Rose Hips and Hibiscus.
Featured items
Alice's Cheddar Jack Toastie (VO) °°°
The classic taste of Cheddar Jack in a warm, toasty panini. You can even add a juicy slice of tomato, if you like. Also available as a VEGAN ALICE!
Deep Dish Oreo Sugar Cookie (V)
House made Deep Dish Sugar Cookie with crumbled Oreo crust and topping. Fully Plant Based! Order by the dozen on our website!
Smoked Robinson °°°
"Get Ready" for a "Quiet Storm" of Country Ham & Smoked Gouda, topped with a Hot Honey Dijon, made with AR's Hot Southern Honey & Grey Poupon! Now that's "Sweet Harmony" (ok, no more Smokey Robinson puns, LOL)!
Rosemary Focaccia Breadsticks & Tomato Soup (VO) °°°
A cup of Tomato Basil soup and 3 Rosemary Focaccia Breadsticks, with Olive Oil and Parmesan. Available without the Parmesan, for Vegan.
IMPOSSIBLE Chopped Cheese (VO) °°°
It's a beautiful thing! Broiled Impossible Burger, chopped & seasoned, smothered with Cheddar Jack Cheese, and topped with your preferred condiments & toppings.
Garden Pasta Salad - 8oz (V) °°°
Ghost of Baby Sis
It's like the Smoked Out Baby Sis, except SPOOKY 👻 Birdie's Ghost Pepper Pimento Cheese, Caramelized Onions, and Fresh Tomatoes.
Brooklyn (VO) °°°
No sleep till Brooklyn! A little Mozzarella, a little Provolone, and a lotta Pepperoni (beef & pork, or veggie), topped with a house made Marinara.
Baby Sis °°°
This little bundle of deliciousness is Pimento Cheese by Birdie's of South Hill, VA, topped with Pickled Jalapeños, and Fresh Tomatoes. Or try the Smoked Out Baby Sis, featuring Birdie's Smoked Gouda Pimento, caramelized onions, and Fresh Tomatoes!
Ms. Pam's Tuna Melt °°°
Bluefin Tuna Salad, with Duke's Mayonnaise, and Extra Sharp Cheddar. Plant based cheese available!
SPOOKY FEATURES 👻
Tradition - Persnickety Witch Pumpkin Ale - 5.8%25 ABV - 16oz Can
A milder style seasonal brew offering flavors of cloves, and cinnamon with a caramel undertone. It has a great balance of flavors making it an approachable beer for everyone.Drink up Witches!
Ghost of Baby Sis
It's like the Smoked Out Baby Sis, except SPOOKY 👻 Birdie's Ghost Pepper Pimento Cheese, Caramelized Onions, and Fresh Tomatoes.
CUPS OF SOUP
Cup of Tomato Basil Soup (V)
PANINI MENU
Alice's Cheddar Jack Toastie (VO) °°°
The classic taste of Cheddar Jack in a warm, toasty panini. You can even add a juicy slice of tomato, if you like. Also available as a VEGAN ALICE!
The Duval Sisters °°°
Say hello to Alice & The Aunties! A Grilled Trifecta of Cheese, with Sharp Cheddar, Provolone, and Mozzarella, topped with Bacon Jam.
Brooklyn (VO) °°°
No sleep till Brooklyn! A little Mozzarella, a little Provolone, and a lotta Pepperoni (beef & pork, or veggie), topped with a house made Marinara.
Ms. Pam's Tuna Melt °°°
Bluefin Tuna Salad, with Duke's Mayonnaise, and Extra Sharp Cheddar. Plant based cheese available!
Baby Sis °°°
This little bundle of deliciousness is Pimento Cheese by Birdie's of South Hill, VA, topped with Pickled Jalapeños, and Fresh Tomatoes. Or try the Smoked Out Baby Sis, featuring Birdie's Smoked Gouda Pimento, caramelized onions, and Fresh Tomatoes!
Smoked Robinson °°°
"Get Ready" for a "Quiet Storm" of Country Ham & Smoked Gouda, topped with a Hot Honey Dijon, made with AR's Hot Southern Honey & Grey Poupon! Now that's "Sweet Harmony" (ok, no more Smokey Robinson puns, LOL)!
Turkey & Swiss (VO) °°°
Sliced Turkey and Swiss, with your choice of toppings, finished with your choice of sauce.
Fatboy Basquiat (Roast Beef & Cheddar) °°°
Sliced Roast Beef and Cheddar, with your choice of toppings, finished with a House Made Horseradish Sauce.
IMPOSSIBLE Chopped Cheese (VO) °°°
It's a beautiful thing! Broiled Impossible Burger, chopped & seasoned, smothered with Cheddar Jack Cheese, and topped with your preferred condiments & toppings.
Billie's Holiday (VO) °°°
Baby Bella Mushrooms, Roasted Bell Peppers & Onions, and Mozzarella, with your choice of Dukes Mayo or Vegenaise. Also available with Plant Based Cheese!
QUICK BITES
Rosemary Focaccia Breadsticks & Tomato Soup (VO) °°°
A cup of Tomato Basil soup and 3 Rosemary Focaccia Breadsticks, with Olive Oil and Parmesan. Available without the Parmesan, for Vegan.
Garden Pasta Salad - 8oz (V) °°°
Route 11 Potato Chips (VO) °°°
Red Cabbage & Red Onion Slaw - 8oz °°°
Slaw made with Red Cabbage & Red Onions, pickled in house.
DIPPING SAUCES
Add Dipping Sauces!
SWEET TREATS (VO)
Sugar Cookie (V)
House made Sugar Cookie!
Deep Dish Oreo Sugar Cookie (V)
House made Deep Dish Sugar Cookie with crumbled Oreo crust and topping. Fully Plant Based! Order by the dozen on our website!
SPECIALTY DRINKS
Ginger Blossom
Similar to our BiggAzz Mimosa, but made with Ginger Beer (non-alcoholic) instead of Cuvée. Choose your Nectar, Peach, Mango, or Pear.
Ninja Kombucha - Dry Hopped Lemon Ginger - 12oz Can
Ninja Kombucha - Peach Mint - 12oz Can
Ninja Kombucha - Cranberry Lime Ginger - 12oz Can
Ninja Kombucha - Pineapple Cinnamon - 12oz Can
BEVERAGES
Bottle of Water °°°
Mexican Coca-Cola °°°
Bottle of Sweet Tea °°°
Bottle of Unsweetened Tea °°°
Boylan Ginger Ale °°°
Boylan Grape Soda °°°
Boylan Orange Soda °°°
Boylan Cream Soda °°°
Boylan Root Beer °°°
Boylan Creamy Red Birch Beer °°°
LUNCHBOX COMBOS
Alice LunchBox (VO) °°°
The classic taste of Cheddar Jack in a warm, toasty panini. Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
Duval Sisters LunchBox °°°
Extra Sharp Cheddar, Mozzarella & Provolone, topped with delicious Bacon Jam! Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
Smoked Robinson LunchBox °°°
Country Ham & Smoked Gouda, topped with a Hot Honey Dijon. Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
Brooklyn LunchBox (VO) °°°
Mozzarella, Provolone, and Pepperoni (beef & pork, or veggie), topped with a house made Marinara. Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
Turkey & Swiss LunchBox (VO) °°°
Sliced Turkey Breast and Swiss. Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
IMPOSSIBLE Chopped Cheese LunchBox (VO) °°°
It's a beautiful thing! Broiled Impossible Burger, chopped & seasoned, smothered with Cheddar Jack Cheese, with your choice of toppings. Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
Fatboy Basquiat LunchBox °°°
Sliced Roast Beef and Cheddar, with your choice of toppings, finished with a House Made Horseradish Sauce. Served with a FULL Cup of Soup, Chips, or Slaw, and your choice of drink, plus a sugar cookie (optional).
Featured items
Alice's Cheddar Jack Toastie (VO) °°°
The classic taste of Cheddar Jack in a warm, toasty panini. You can even add a juicy slice of tomato, if you like. Also available as a VEGAN ALICE!
Deep Dish Oreo Sugar Cookie (V)
House made Deep Dish Sugar Cookie with crumbled Oreo crust and topping. Fully Plant Based! Order by the dozen on our website!
Smoked Robinson °°°
"Get Ready" for a "Quiet Storm" of Country Ham & Smoked Gouda, topped with a Hot Honey Dijon, made with AR's Hot Southern Honey & Grey Poupon! Now that's "Sweet Harmony" (ok, no more Smokey Robinson puns, LOL)!
Rosemary Focaccia Breadsticks & Tomato Soup (VO) °°°
A cup of Tomato Basil soup and 3 Rosemary Focaccia Breadsticks, with Olive Oil and Parmesan. Available without the Parmesan, for Vegan.
IMPOSSIBLE Chopped Cheese (VO) °°°
It's a beautiful thing! Broiled Impossible Burger, chopped & seasoned, smothered with Cheddar Jack Cheese, and topped with your preferred condiments & toppings.
Garden Pasta Salad - 8oz (V) °°°
Brooklyn (VO) °°°
No sleep till Brooklyn! A little Mozzarella, a little Provolone, and a lotta Pepperoni (beef & pork, or veggie), topped with a house made Marinara.
Baby Sis °°°
This little bundle of deliciousness is Pimento Cheese by Birdie's of South Hill, VA, topped with Pickled Jalapeños, and Fresh Tomatoes. Or try the Smoked Out Baby Sis, featuring Birdie's Smoked Gouda Pimento, caramelized onions, and Fresh Tomatoes!
Ms. Pam's Tuna Melt °°°
Bluefin Tuna Salad, with Duke's Mayonnaise, and Extra Sharp Cheddar. Plant based cheese available!
CUPS OF SOUP
Cup of Tomato Basil Soup (V)
PANINI MENU
Alice's Cheddar Jack Toastie (VO) °°°
The classic taste of Cheddar Jack in a warm, toasty panini. You can even add a juicy slice of tomato, if you like. Also available as a VEGAN ALICE!
The Duval Sisters °°°
Say hello to Alice & The Aunties! A Grilled Trifecta of Cheese, with Sharp Cheddar, Provolone, and Mozzarella, topped with Bacon Jam.
Brooklyn (VO) °°°
No sleep till Brooklyn! A little Mozzarella, a little Provolone, and a lotta Pepperoni (beef & pork, or veggie), topped with a house made Marinara.
Brooklyn PLANT BASED (V)
The Brooklyn but VEGAN! Plant Based Mozzarella & Plant Based Pepperoni, topped with a house made Marinara.
Ms. Pam's Tuna Melt °°°
Bluefin Tuna Salad, with Duke's Mayonnaise, and Extra Sharp Cheddar. Plant based cheese available!
Baby Sis °°°
This little bundle of deliciousness is Pimento Cheese by Birdie's of South Hill, VA, topped with Pickled Jalapeños, and Fresh Tomatoes. Or try the Smoked Out Baby Sis, featuring Birdie's Smoked Gouda Pimento, caramelized onions, and Fresh Tomatoes!
Smoked Robinson °°°
"Get Ready" for a "Quiet Storm" of Country Ham & Smoked Gouda, topped with a Hot Honey Dijon, made with AR's Hot Southern Honey & Grey Poupon! Now that's "Sweet Harmony" (ok, no more Smokey Robinson puns, LOL)!
Turkey & Swiss (VO) °°°
Sliced Turkey and Swiss, with your choice of toppings, finished with your choice of sauce.
Fatboy Basquiat (Roast Beef & Cheddar) °°°
Sliced Roast Beef and Cheddar, with your choice of toppings, finished with a House Made Horseradish Sauce.
IMPOSSIBLE Chopped Cheese (VO) °°°
It's a beautiful thing! Broiled Impossible Burger, chopped & seasoned, smothered with Cheddar Jack Cheese, and topped with your preferred condiments & toppings.
Billie's Holiday (VO) °°°
Baby Bella Mushrooms, Roasted Bell Peppers & Onions, and Mozzarella, with your choice of Dukes Mayo or Vegenaise. Also available with Plant Based Cheese!
QUICK BITES
Garden Pasta Salad - 8oz (V) °°°
Rosemary Focaccia Breadsticks & Tomato Soup (VO) °°°
A cup of Tomato Basil soup and 3 Rosemary Focaccia Breadsticks, with Olive Oil and Parmesan. Available without the Parmesan, for Vegan.
Route 11 Potato Chips (VO) °°°
Red Cabbage & Red Onion Slaw - 8oz °°°
Slaw made with Red Cabbage & Red Onions, pickled in house.
DIPPING SAUCES
Add Dipping Sauces!
SWEET TREATS (VO)
Sugar Cookie (V)
House made Sugar Cookie!
Deep Dish Oreo Sugar Cookie (V)
House made Deep Dish Sugar Cookie with crumbled Oreo crust and topping. Fully Plant Based! Order by the dozen on our website!
SPECIALTY DRINKS
Ginger Blossom
Similar to our BiggAzz Mimosa, but made with Ginger Beer (non-alcoholic) instead of Cuvée. Choose your Nectar, Peach, Mango, or Pear.
Ninja Kombucha - Dry Hopped Lemon Ginger - 12oz Can
Ninja Kombucha - Peach Mint - 12oz Can
Ninja Kombucha - Cranberry Lime Ginger - 12oz Can
Ninja Kombucha - Pineapple Cinnamon - 12oz Can
BEVERAGES
Bottle of Water °°°
Mexican Coca-Cola °°°
Bottle of Sweet Tea °°°
Bottle of Unsweetened Tea °°°
Boylan Ginger Ale °°°
Boylan Grape Soda °°°
Boylan Orange Soda °°°
Boylan Cream Soda °°°
Boylan Root Beer °°°
Boylan Creamy Red Birch Beer °°°
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Recent Reviews
This place isn’t talked about enough. Great soups, grilled cheese and vegan options. Crab bisque is a tad on the salty side but still great. Sandwiches are the perfect size and delicious. Will definitely order again
December 2025
I absolutely LOVE this gem. Found it 3 years ago suggested by locals while I was visiting Richmond. I've made it a point to go back every single time when I'm in town each consecutive year. My only wish is that they had a bowl of their tomato soup side available as it is so delicious! My coworker and I look forward to eating here and patiently wait all year for October to roll around 🤤
October 2025
Tasty but salty basic grilled cheese on a panini press, and variations of grilled cheese with chicken on it.
Best feature is a vegetarian chicken option (and vegan cheese if you need it). Sandwiches currently $8 to $15 as of summer 2025. Limited drink options.
No place to sit inside, so take out or sit at one of few tables on the sidewalk; no umbrellas for sun protection.
Staff pleasant.
Best feature is a vegetarian chicken option (and vegan cheese if you need it). Sandwiches currently $8 to $15 as of summer 2025. Limited drink options.
No place to sit inside, so take out or sit at one of few tables on the sidewalk; no umbrellas for sun protection.
Staff pleasant.
August 2025
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