Favorite Bars in Portland, Conn.

Eating and Drinking in Portland, Conn.

Portland, Conn. is a small town, it is hard to imagine that a place this small would have three good bars. It says a lot about a place when the quality of the bars far outstrips almost everything else. Here are three of my favorite bars in Portland, Conn.

Winchester Cafe

Our favorite of the three is the Winchester Café. Café is a bit classier sounding than the place actually is. It is much more of a biker bar than a café but having said that, it has a warm and welcoming atmosphere, good food, lively entertainment and karaoke.

The clientele is varied. You are as likely to see grandparents as you are young folks. When the weather is good, you will see a lot of bikes lined up out in front. There is a small outdoor patio area where the smokers tend to congregate since you can’t smoke indoors in Connecticut.

If you are looking for a fancy martini, this is probably not the place for you. Come here for a cold beer, a good quality whiskey on the rocks or a rum and coke. You can sit at the bar or head to one of the booth. There is a pool table for those that feel like running a rack and two TV’s are going all the time. 

On Thursday, Friday and Saturday they serve a great prime rib which believe it or not is why we usually come here. They also serve Buffalo burgers and a very nice patty melt.

Farrell’s Restaurant

Farrell’s is an institution in Portland, Conn. It is an Irish bar and restaurant. This is the main gathering place in town. Many locals would never consider going anywhere else. The bar is very popular and you will almost always find every seat at the bar filled. They have a couple tall, round bar tables and booths. If you want to see the real microcosm of Portland this is the place to do it. In the restaurant the businessmen will be having a meeting and in the bar area the rest of the town is hanging out.

The food is good here, steamed cheeseburgers, generous appetizers as well as tasty salads and sandwiches. You can have a loaded plate with fajitas, meatloaf or a steak. You will find families, seniors and just about anyone in town hanging out here on any given night.

If you have never tried a steamed cheeseburger, you need to give it a try. You can get your favorite fancy drinks here as well as a nice selection of wine and beer both on tap and in the bottle.


Campagna is the newest entry in the bar stakes. They have a separate bar area where we play cards every Monday night. The restaurant is upscale but the bar is cozy and friendly and you can get a good selection of great drinks and specials. They have a Facebook account, that tells you something. The food is Italian with a twist.

As you can see, for a town with less than 8,000 people, Portland has its share of places to get a good drink, meet the locals and enjoy some good food too. These three are our favorite bars in Portland, Conn.

Share with your friends
To report this post you need to login first.

Leave a Reply

Your email address will not be published. Required fields are marked *