Honestly you'll find many discussions here about favorite heirloom, best heirloom, favorite open pollinated (since they aren't always heirlooms), etc. I linked one of them below.

And lots of discussions about how taste/flavor is a very subjective thing and varies greatly from person to person and from garden to garden since growing conditions control much about taste.

So what you will get is just personal opinions on favorites based on how each person defines "old fashioned flavor". The usual recommendation is for those new to them to try several and see which ones they prefer when grown in their own garden soil and growing conditions.

Assuming that is what you are looking for then my personal favorites do NOT include Aunt Ruby's and especially not Green Zebra (I think its safe to say that not many would consider it a fav) but I would include Cherokee Purple.

But most of my personal favorites would not be the different color heirlooms/OPs but the plain old reds and pinks like Box Car Willie, Mortgage Lifter, Rutgers, Brandywine (any variety), 1884, Aker's West Virginia, Eva Purple Ball, and Earl's Faux just to name a few.

Of course if you are dependent on growing from transplants rather than from seed your choice will be severely limited. If growing from seeds then there are a thousand to pick from and Carolyn's book 100 Heirloom Tomatoes for the American Garden, by Carolyn J. Male is a good place to start exploring the choices. You can also check out 100s of heirloom varieties at tomatofest.com

Dave

Here is a link that might be useful: Best Heirlooms discussion

Thanks for the resopnses. Cherokee Purple seems to be the clear winner so far--good thing my local nursery had it.

Brandywine is my favorite for good old fashioned tomato flavor, and Kellogs Breakfast for taste if you don't mind an orange tomato. Cherokee Purple is always in my garden, good taste and reliable, but not what "I" consider traditional tomato flavor. I think purples and blacks taste a little different than traditional reds or pinks. But KB certainly isn't one of those either. All are in my list of favorites. Brandywine is probably more what I think of when I think good old fashioned tomato flavor.

I remember setting out young tomato plants when I was in grade school. You know back when we walked to school bare foot in the snow up hill, both ways.
But never heard of heirloom until I was a organic gardener.
We just had good tomatoes & better tomatoes.
My father was a natural gardener who used 10-10-10- & manure to get the best the land would give.
Raised on cornbread,black eyed peas & mater sandwiches.
* So what is a heirloom tomato & how do I know that is what I am getting?
Like the word "ORGANIC", sometime the name Heirloom is just to charge more for the already over priced seeds.

Don't miss out on Aunt Ruby's German Green - it is a very nice flavored tomato. Cherokee Purple is also very good. Both do well in my Zone 4 garden. We really like Kellogg's Breakfast - it is just scrumptious.

If you like a zippy kind of tomato flavor, you might like the Green Zebra. Some folks grow it exclusively though I personally cannot figure out why. It is tart IMO.

You must be purchasing transplants as it would be very late for you to start from seed in your area.

Cherokee Purple is #1 in taste and productivity. My crop this year, CP, Brandywine pink and red,Pineapple, Black Prince, German Johnson, Golden Egg, Prudent Purple, Abe Lincoln, Amish Paste. Still searching for one that equals CP.

As digdirt said, these wouldn't be varieties that I would associate with "true tomato" flavor.

That said, I love Cherokee Purple (on the sweeter side of "true tomato" flavor...which I like) and Aunt Ruby's Green (also very sweet, even more so than CP).

And "Gold Medal" fans?

Speaking of Mortgage Lifter(my favorite so far), garden centers in my area are beginning to sell an improved(hybrid) Radiator Charlie ML. But Estlers ML is a better tomato than the Byles variety heirloom or improved. I am growing Pink Pounder and Brandy Boy also for comparison but I do like the better size of the ML but taste is imp too. Growing Cherokee Purple for the first time and Portehouse as well. Spent time today moving 27 seedlings in and out of the sun(whats that right?)Really anxious to get started in the garden. Have some container stuff started but I NEED to get behind that tiller and get my knees dirty. Dig?

I'm sheepishly adding that I actually love Green Zebra (sorry GZ haters...LOL). I grow them every year in addition to 12 other varieties. I think they are fresh and citrusy, but I would add that they are not a "typical" tomato flavor. I love them in recipes where a little more acidity is called for. And they make a beautiful addition to a mix with other color tomatoes. I would agree with Dave that tastes are very subjective. I'm a big fan of Cherokee Purple, and in fact I tend to prefer the purple/black tomatoes. Their flavor is really complex and full. I'm growing 4 varieties of blacks this year. Brandywine is obviously a classic when it comes to traditional tomato flavor, but I think they are a little tricky to grow and not always very high producers. I'm cutting them from my list this year for the first time in 10 years. Instead (for Reds) I'm growing coustralee and Goose creek which I love, and Marrianna's Peace (first time, but I hear great things). But I suggest you try'm all for yourself. When I go to the farmer's market in the seasons before my own tomatoes are ready I always ask them what varietes they are growing and try and taste as many different ones as possible.
Don

I agree with the Cherokee Purple and Brandywine crowd. I also like to add a heart shaped tomato like Anna Russian, which tastes great and ripens early. Also what about Stupice or Matina. Small, early, and talk about true tomato flavor! I think I am biased towards Stupice because it's usually the first tomato I get to eat each year. As far as color goes I'm a fan of reds, pinks, and black/purple. I like sweet tomatoes and I'd also be a bi-color (Hillbilly West Virginia) fan if I could ever get one to ripen properly. Just not a fan of orange, yellow, or green. But that's just me.

I did not grow from seed this year (had a terrible year last year when I did ... and hello from the past, it's been years since I've been on this forum). That said, I bought 10 different heirloom varieties from two local nurseries, seven of which are in Dr. Carolyn's book. It may just be in California, but I had a nice selection of plant starts this year.

I could be wrong, but it seems like Heirlooms and OP's are showing up more at nurseries/garden centers in the last few years. I never remember seeing Cherokee Purple, etc. at these places years ago. They must be becoming more popular.

ladon,
a few years ago I helped organize a tomato tasting here in Sacramento(I think there might still be photos up at another tomato site.) We had a huge number of varieties(from just a few very enthusiastic growers) and surprisingly the Green Zebra was rated highest that day. It's a great variety.

If it is nostalgia for a certain flavor that motivates you, it depends on what type of tomatoes were in vogue when you developed a taste for them. For me, that would be the 1940's. That was a time when tomato research at state universities had peaked, resulting in varieties such as Rutgers and Wisconsin 55. It was the start of the era of hybrid and "low acid" varieties. For you, tomatoes of a different era may taste "old fashioned".

The problem is confounded though by changes in our taste as we age and by the vagueness of taste memory. I have discovered some good tasting tomatoes but haven't found the taste I remember.

Jim

I bought my first Cherokee Purple from Target about 10 years ago, edweather. It was a giant plant in a gallon size container with fruit already set on it, so that Cherokee Purple was the first (very delicious!) fruit of the season that year.

I grew my first heirloom tomatoes last year after reading about the flavor of Cherokee Purple. Although it was the worst tomato year ever here I managed to get about a dozen vine ripened Cherokee Purples, up until then I'd always grown nice red smooth fruiting tomatoes. The other varieties I had didn't produce any fruit, yep a really bad tomato year for me.
I can't say they were the prettiest tomatoes by a long shot in fact at first I slapped the top piece of bread on a sandwich toot sweet, being so used to those beautiful red slices LOL. Mmmmm just thinking of the flavor of this tomato has me salivating, I can hardly wait for this years crop.

I gave a few plants to my neighbor to try, he had better luck then me, he had his tomato bed against a south facing concrete wall. His wife took one look at them growing and said I'm not eating that, what's wrong with it. One day he got her to shut her eyes for a taste test, after about the third bite of others he was growing he slipped her a piece of Cherokee Purple, she loved it so much it's going to be their main tomato this year, us too.

Annette

As someone that grows hundreds of heirloom tomatoes every year, I must admit I no longer grow any of those listed by Girlbug2. We all have our favorites and they will vary as much as those who answer.
I would have to say that my favorites are Brandywines. I'm especially fond of Cowlick's Brandywine, Brandywine-Glicks, and Brandywine-Sudduth's. I also like the Brandywine/Cherokee Purple crosses like: Liz Birt, Dora, Bear Creek and Gary O'Sena. I find thee crosses to be both better tasting and much better producers than Cherokee Purple itself. Also much more consistant in taste and having a longer shelf life.
I'm also quite fond of a few others that I find outstanding here in south central Pa. In pinks:
Barlow Jap
Sandul Moldovan
Mrs Benson
Lillian Maciejewski's Poland Pink
Earl's Faux
Ed's Millenium
Rose
Limbaugh's Legacy Potato Top
Stump of the World
and all the pink Brandywines.
In Black/Purples:
Amazon Chocolate
Dana's Dusky Rose
Blackmaster
Swisher Sweet
JD's Special C-Tex
Indian Stripe
Shannon's South African Mystery Black
and the aforementioned Bear Creek and Gary O'Sena
In Reds:
Tarasenko6
Gigantesque
Preacher Joe
Box-car Willie
In orange/yellow/gold:
Kellogg's Breakfast/KBX
Dr. Wyche's Yellow
Lillian's Yellow Heirloom
in GWR:
Cherokee Green
There are others, but these are the best of the best for me over the past few years and most of what I'm growing this year along with a few new to me varieties and a few that did well for me in the past and deserve another try, like Black Brandywine, Pink Sweet, Royal Hillbilly, and German Johnson-Benton strain.
I hope whatever ones you try do well for you and you discover the wonderful world of Heirloom tomatoes.
Enjoy!
Camo

I grew Gold Medal, Cherokee Purple and Brandywine Sudduth last year. Surprisingly Brandywine was my most productive. Cherokee Purple was the only one with a significant cracking problem (my friends kept calling them the ugly tomatoes).

In terms of taste, Brandywine was hands down my favorite, especially toward the mid and late season. The fruits were sweet, perfect texture, juicy, the way I remembered how tomatoes tasted when I was a child. Gold Medal was not as sweet as Brandywine, but it had a silky smooth texture and the fruit was beautiful. Cherokee Purple was a bit bland imho. So this year I am skipping Cherokee Purple and only growing the other two for the main crop.

I GUESS it is all a matter of taste...each one of us has an individual like or dislike. Aunt Ruby's German Green is one of my favourites. It is beautiful to look at, slices well, and tastes fantastic..not too sweet..just right. Cherokee Chocolate is a fav. to. as well as Marizol Purple, and Sudduth's B.W. This year I have cut down my quantities of plants to give the garden a break...cheers martha/zucchini