The Caboose Market & Cafe — Restaurant in Ashland

09/08/25 This is becoming a very good habit. Last night The Caboose market and Café hosted their first wine dinner of the year. This is what Nick and his team have been working towards all year long. Although this was Kenny’s (The Chef) first wine dinner, expectations were high. Kenny and his culinary wizards have been consistently knocking it out of the park. Last night Kenny cemented his place as one of the best at The Caboose and here in the center of the universe. Congratulations! Especially thanks to David O’Neill, the evening’s sommelier. Your wine selections for each of the entrées were perfect. Thanks for a perfect evening Nick!

08/27/25 I am so sorry you missed it! Kenny and his team of culinary magicians were at it again. Tonight’s date night special: @charityhillfarms braised chuck roast, braised potatoes and mixed veggies, served with a mushroom demi. Total awesomeness! Love the coveralls Britney!!

This will be a very fun review. Am I a little biased? Absolutely! I have been dining at The Caboose Market and Cafe for over 10 years and that is definitely for a good reason. There is always something happening at The Caboose. Be on Sloppy Joe Tuesdays, Wednesdays Date Night, Wine tap take over Thursdays or Friday night pizza (last Friday of the month) you’re bound to have an excellent evening at The Caboose.

My favorite evening, Date Night. Michele and I have been enjoying Wednesday Date Night for a little over five years now. It never seems to get old! The menus changed duringspring and fall, and the Wine selection is always fresh. Appetizers include a selection of cheeses and meats. The main dish is either gourmet salads or sandwiches. My favorite is adding steak to my salad. Finally the date night dinner is capped with a dessert. Don’t miss out on the apple cobbler and ice cream!

If all you seek is Wine or beer, the selections available at The Caboose are outstanding. Every Friday evening The Caboose invites a sommelier to provide a wine tasting. What better way to learn about wine.

Finally, I can’t say enough about the staff at The Caboose. They have this chemistry about them. They absolutely enjoy what they do.

05/14/25: Caboose Chef has outdone himself once again. Wednesday date night special. Wow.

05/28/25: Where’d that chicken grow up!? Kenny knocks it out of the park once again. Delicious Chicken Cordon Bleu on a bed of creamy risotto. Awesome.

07/11/25: yeap… Pizza night (1st Friday of the month). Orders for your choice of meat or veggie pizza can be made starting Thursday at 11:00. The Caboose was packed this evening. Congratulations to the Caboose team for another fantastic evening.

07/23/25: Kenny strikes again! Wednesday Date Night special: Braised @pink.housefarms pork over cabbage and house made @labellavitabakery garlic bread dumplings. Dude! That...

I was surprised last Monday, October 25th, 2021, to find myself dining in The Caboose Market and Cafe. I had not been in Ashland, VA, since 2017, and I had returned hoping to dine once more with the lovely owner of Monique’s Crepes at her mobile site. But on this occasion she had slipped away—I don’t THINK she knew I was coming, but she may have good radar—and so, thank heaven for the opportunity to dine in the Caboose!

If you have not been to Ashland, you will enjoy your visit: it is a very pretty college town, where almost everything seems to be within walking distance—although you must dart or drive back and forth over the active railroad tracks that cut the town virtually through the middle! Ashland’s embrace of the railroad seems wholehearted, and it enjoys at least two visits daily of the beloved Amtrak commuter.

But you are hungry—or seeking wine or cheese: and as I did Monday, you have come to the right place! Pricey but classy, The Caboose will entertain you whether as Parisian style you dine al fresco beside the neat tracks of the local chemin-de-fer, or in the cosy deep interior dining area in the rear. “You can get most anything you want” here, and most anything you order will be splendid. Everyone is very friendly and helpful: if the cleverness of the menu is a little puzzling, your waiter will take time with you to ensure you get precisely what you want. It is even easy to strike up a conversation with the locals—I enjoyed a long and enjoyable chat with a lovely couple on the history and memories of Ashland—which had changed impressively even in the four years I had been away!—One of the impressive changes being the expansion of the restaurant we were enjoying into its present and very beautiful butterfly! I include—as I try to nowadays—a number of...

So I love this place but had one draw back. I arrived to eat lunch after having two amazing breakfast's there. This time I had my autistic son with me. When I inquired what kind of food they had that my son would eat, because he like most autistic children has texture issues. I was met with an answer that made me feel like i somehow was not wanted there...i asked do you have French fries and the older waitress responded with "there is a place across the street that serves burgers and fries, this place is not for everyone". She then said the same thing to my girlfriend when she arived shortly after as she stopped in the bathroom before sitting. TWICE she felt the need to make me feel like i wasnt welcome in her little world. Excuse me lady but me inquiring what foods you have that my son will eat does not give you grounds to make us feel like we are not open minded or trendy enough for your establishment. She then continued her rudeness throughout our meal bringing me things and setting them on my table like she was mad at us for just existing. I continued to say thank you and she acted as if she did not hear me. I'm so torn because the younger waitress is nice and helpful every time I come. The food is amazing and I have not had a single thing that I was not impressed with. I will be contacting the owner because I believe that this place is a little diamond that more people should try. Food good!! Waitress that took every opportunity to make my family and i feel...