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Blaze Your Trail for Good Times at the Winchester Cafe

Bar & Restaurant in Portland, CT Resembles an Old Western Saloon

Stepping into the Winchester Cafe is like stepping back in time. The obvious reason is the atmosphere of the Winchester suggests an old western saloon of movie days. We display old wagon parts, lamps, and pictures that are reminiscent of those days.

The secondary feeling of nostalgia occurs because many of you have a vague memory of hot dogs and milk shakes purchased here when it was a smaller building known as Walt's. We invite you to read more about the history of the Winchester Cafe.

We have full liquor service and a long bar that seats quite a few patrons. Everyone loves our "cowboy" bar stool shaped like a saddle. We also have a menu with everything you'd expect in a place with an old west atmosphere. We never do fast food here. Hot food is sizzlin' the old fashioned way. Cold food such as salads can't get any fresher.

If you like to have fun and enjoy music when you go out, we have a pool table for starters. We've scheduled live bands, cruise nights and karaoke, too. Go to our happenings page for more information. 

We also have some art work and western articles for sale in the "back 40" of the bar that might be of interest.

We hope you'll enjoy your visit with us and that you, too, will become
a "Winchester Repeater"! Get directions if you haven't been here yet. 
Good times with a bang at the Windhester Cafe, Portland, CT
"Wisdom from the Trail," a page of quotations on the Winchester Cafe menu.
2nd place winner New England Chile Cook-off
Are You Hungry Yet?
The Winchester Cafe is open 6 days a week.
Tuesday thru Thursday
11:30 A.M. - 1 A.M.
11:30 A.M. -
2 A.M.
Noon - 2 A.M.
11 A.M. -
11 P.M.
Copyright © 2011-2021 by the Winchester Cafe

Painting of a cowboy and dressed up lady in a western saloon on display at the Winchester Cafe
Visit Our Photo Gallery
1374 Portland Cobalt Road, Portland, CT 06480   860-342-0224   Get Directions
Don't Miss Our
Lineup of Bands
It's Live Music
at Its Best at the
Winchester Cafe
Go to Happenings for Details
We're Ready for Car Show Season at the Winchester Cafe!
The Winchester Cafe is on Route 66 in Portland, CT
Portland, CT
Karaoke Thursdays and 1st - 3rd Saturdays starting at 8:30
We Will Have a Band on the Last Saturday of Every Month

our next open mic with North Cove Rogues will be Wednesday, August 19th, starting at 7:00.

CHRIS and ROLAND 1st Sunday of Every Month
Throughout the Summer
Fun at The Winchester Cafe Is Coming Up!

​Saturday Sept 19th---Cruise Night--Raffles! Prizes! Classic cars! Dash plaques! Drink discounts!Raffles to benefit Portland Food Bank
Winchester Cafe in Portland, CT since 1982
The old Western saloon atmosphere is a must see at the Winchester Cafe
Half price apps from 4:00-7:00 Tuesdays thru Thursdays. The perfect special for after work.
*New Special
The old Western saloon atmosphere is a must see at the Winchester Cafe
Raffle winners, drink specials, dash plaques for first 50 cars and a winner of a $50 gas card.
Stop in for daily lunch specials!