Oscar’s Delicatessen

Oscars is simply overpriced, and not that well kept up.
Their service is fast, but product quality rather bland, and you feel pressured to order fast. Just nothing special, and then prices are quite high, so it just doesn’t work for me. Pass on the $ 3.00 cookies as well. This place thrives on location, but otherwise not much going for it.

First Class Deli food. Freshly prepared to order. Delicious pastrami, corned beef. Take out or eat in. Sidewalk or air conditioned inside tables. Recommend.

Solid Jewish style deli.
No frills.
Whitefish salad.
Hebrew national products.
NY style bagels & cream cheese,
Lox, capers– the traditional works.
Matzoh ball soup.
Hot/​cold food.
Thick deli sandwiches.
Variety of chips, sweets, candy & obscure rare old school novelties.
Indoor/​outdoor seating.

I’ve been coming to Oscars off and on for 30… never by choice, but because people heard about it and HAD to try it. I was never impressed. Sandwiches are bland, service is horrific, pastries obviously come from some industrial «bakery» someplace else and everything is overpriced. Until I tried their chicken wings this last week, I was willing to let tourists take their lumps, but am now compelled to speak. Hold on to your stomach…
I seriously suspect the chicken wings are precooked, probably boiled somewhere, then frozen, then left to thaw at Oscars in the window. When they heat them up, they put them in a microwave for 40 seconds and come out hideous.
From the cookies to the sandwiches to what they shovel into their front window, avoid this place, and keep driving up the Post Road.

Oscars Deli has been a favorite place for high quality deli food for 45 years. The owner Lee is a great guy with a fun personality. The staff there are great people who warmly welcome all customers. And the bowl of pickles on the table are the best.

This is an absolute MUST stop every time I take a trip out to the east coast! A bowl of pickles and a sandwich big enough to feed a small army… come on! The food is delicious, the staff is incredibly friendly and the price is right. And their cookies are well worth saving a little room. Just go and enjoy yourself, then tell all of your friends to do the same. Yum!

I prefer Gold’s deli. Love the pickles with every order. But don’t like that they make the sandwich then touch the money. Just don’t think it’s hygienic.

Oscar and Sally; ’nuff said.

I love the corned beef sandwiches with cole slaw and russian dressing!
When I am missing NYC, I stop by and have that for lunch!
then I head back to school.
The staff behind the counter is always friendly, and fast !

This USED to be the best Deli in Westport. Not anymore. Art’s Deli is clearly better. The sandwich makers are surly and unhelpful at Oscar’s too, BIG minus.

best matzoh ball soup in town!!!

A downtown Westport favorite, friendly. Food is just average and the prices have become outrageous.

Yummy, huge sandwiches but pricey.

Well, it’s not perfect– but it will suit your Jewish-​type-​deli needs. Downtown westport is so cute and this place has a nice selection of hot sandwiches as well as a chicken-​noodle-​matzo ball soup. Definitely a mile above any Sandwich chain.
I don’t generally frequent the bakery items, just soup and sandwiches and free pickles for us. They do have a large amount of bakery items (cookies and the like) but I can’t vouch for their goodness.

Oscar’s is one of those neighborhood deli shops that has everything you could ever want in a small store. Six giant beverage cases running the gamut in thirst-​quenching, from Coca-​Cola to that new-​fangled Snapple you’ve been seeing commercials that advertise the «good stuff.» They’ve got benches and chairs a plenty, a plethora of PEZ (complete with collectible PEZ dispencers in cartoon characters like Batman and Mickey Mouse) and more chips than I hope you’d ever consider eating.
Though I did not grow up here, nor am I even remotely from here, I could tell Oscar’s has been around for a long time. From local art and photography on the walls, to murals depicting a scene of neighborhood regulars at a counter-​top establishment, to the taped-​up pictures of family behind the counter. There’s a quirkiness to it that is lived in and familiar, just like the hand-​written sayings taped inside of the napkin dispensers on each other tables. Random, but funny.
For sustenance, I chose the Harry and Sally Special (essentially a BLT with smoked salmon on toasted wheat bread) and a Green Tea Snapple (made with real sugar, quite good). The total was $ 12.80, an amount I’d normally pay for a sandwich and a soft drink at pricey spot on Newbury Street or the Financial District, not suburban Connecticut. Though I was a little miffed by the price tag, I cannot deny a well-​made sandwich. Proportioned, perfectly toasted, light on the mayo and anything-​but-​skimpy with the salmon – there was a ton of it! I could have done without the pickle, which was hardly deli style.
Though I most likely won’t be venturing back to Oscar’s anytime soon (as it’s not on my way to anywhere) that doesn’t mean you shouldn’t check it out. There’s a sandwich for everyone’s taste and they even have some baked goods.