Where to begin

I started last year totally green - never competed in anything remotely close to a triathlon.  I used to bike a lot (off road) and learned to swim while in Dubai, so with very limited experience I did the following:
Warren Eco Friendly Sprint Tri in June - killer hill at the end of the bike and hilly run
Mossman Sprint Tri in July - huge event, tons of fun
Niantic Bay Sprint Tri in August - tons of fun, flat, I actually tried this in 2009 as a test run.
Madison Sprint Tri and Kiwanis (short sprint)in September - Madison is flat and fast, end of season - could be kinda cool.  Kiwanis is really too short - 5 mile bike and only a 2.5 mile run

Also from June 15 to August 21 I did 9 of the 10 Farmington off-road tri events that were an AWESOME distraction from the normal routine.  You will learn so much about how your body reacts during an event since you do the same exact event 10 times.  You test how you react to eating or drinking (even though its a short course and you learn not to even bother with it) and it helps you develop transition technique.

These kept me busy and was enough proof for me to believe I could tackel an olympic this year.
So this year I plan on the Pat Griskus and Timberman and will delete one or two of the Sprints.

The energy around the triathlon world is so "positive" I am totally hooked on it and will continue as long as I can.  Good luck with your adventure.

I guess my post doesn't really answer your question that well, so a little more data here from my experience:The Warren even in June was my fastest swim all year so I think it was a hair short of a 1/2 mile. The water was surprisingly warm (small lake). The bike starts off with a fast, quick downhill to a loop around a much larger lake, then back up hill to the smaller lake, and when I say up hill, I mean 1st gear pushing hard for 1/8 of a mile on a steep climb. Then the run is a small (1/8 mile) trail run to the paved road down the hill and back up. The event took place AFTER work on a friday night, which was a great excuse for me to get out early. Pre and post events were great, well organized.The Mossman seemed like the most professional event. Very official check in, LOTs of competitors, well run, nothing surprising at all. Flat bike and run. Average post race activity.I did the Niantic Bay twice, both times the event was well run, organized, average post race event, full 1/2 mile swim, flat bike and run.Madison was similar, slightly more hilly on the ride, but not hard. Nice run. The swim was at low tide so you could litterally run 10% of it if you wanted to. Post race was okay, since it was so late in the summer, the wetsuit was welcome early in the morning.Kiwanis in Norwalk - a great beginner/family event.

For a late season half ironman, check out Ironman Poconos. It is the first weekend in October. I don't remember the cost, but it is late enough in the season so you can probably register for it after you try one triathlon in the spring. This will be the first year for the event and they haven't posted the course maps yet - but I'm hoping it is a good one as it will be my first half. For other events, there is a sprint in Bridgeport mid-June sponsored by Tri-fitness which could be a good first event. The swim is in the sound and I have heard that the bike and run are flat and fast. There is an Olympic in stamford later in June. Those are my first two triathlon events for the coming year. Best of luck.

early season sprint: Mystic.  Small local, registration usually opens in march for first week of June.  well run, good course, great post race party on the beach.  only draw back is sometimes they mis-time the tide and you have a bit of a mud run

June oly: griskus oly, very hard but great race.

July:  Mossman sprint in norwalk.  gross beach but fast bike and run.  Griskus sprint is on a wednesday night.

August: greenwich sprint.  Mossman oly (super fast course)

September: brandoford and guildford.  Or come out to Marthas Vineyard.

Also, the NEw Haven Road Race is a must do on labor day.

All of the above are very well run races.  No local late season HIMs.  IMRI 70.3 is in july.  Montauk is in October.

Hyannis sprint in June and September is an extremely well run event which is great for beginners and Vets alike. There are about 9 different start waves depending on your abililty. The event is well sponsored, lots of staff as well. Cape Cod in the summer!!  There is even a division for newbies!!

FirmMan Half Ironman in Rhode Island in early September.  

Aaron! How U doin! I've been getting fat and lazy lately. Had my other achilles rebuilt and have just started biking again.no running yet; just finishing my PT regimen. Hope life is treating you well.

Dave

Where are you located (if you add that to your profile everyone will be able to see it)?  That will help us with some recommendations since you probably don't want to drive 3 hrs for a sprint race.

Last year was my first year. I did a lot of sprint racing and planned to race olympic, but had to travel for work during the race weekend.  If you are not confident in the bike/run portion yet, do a bunch of sprint and olympic racing this year.  You will learn a lot and tackle the HIM next year.

I'm in North Stonington, so all of my racing was within an hour of there last year.  Here are some:
Mystic (6/5) - very good for new racers.  It has a very diverse field and the course isn't really challenging. 

Lake Terramugus series - great mid-week racing.  It is very low key and cheap to enter.   It's easy to get good race practice (such as transitions, equipment choices, etc).  You can also do the same race multiple times in the season to try different things and truelly evaluate apples to apples impact.

Niantic - this was the most professional of all the races I did.  There were officials actually enforcing rules (assessing time penalties, safety checking bikes, etc).  Niantic did sell out last year, so don't wait until the end to register.

TriMom events in RI - Crabman Sprint and Oh My Goddard Sprint.  These have even more of a "welcome to the sport" type of atmosphere.

Good luck.

Thanks for all of the input! It's really helpful to be able to put some of these races into perspective and to hear the experiences that others have had as well as course descriptions.

I'm centrally located (Middletown, CT), so that leaves quite a bit open for me in terms of when/where I can race. I can get to most major highways easily and reach most parts of the State in an hour or less. 

Thanks again!

I would 2nd the Terramuggus. Last year they stretched the swim out to 600 yds, it's a very hilly bike/run course. It's really almost a full sprint and it happens every other week. Combine that with some of the Farmington off roads - quick swim, but super super fun bike and then a trail run. I'd just throw in one or two others and you can get thru the summer with only a few hundred bucks in entry fees.

Being from Middletown, i would recommend either the Griskus sprint or OLY at Quassy, very well run.
I don't love the run, but swim and bike are good.

Rev3's sound great too, but are very pricey.