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Fairfield vs New London - New London is a very unique small town, but I cannot take it over Fairfield unfortunately. Fairfield is such a well rounded town with one of the best beaches in the state, lots of amenities, and some very pretty rural upscale areas.
Chester vs Washington - This one is EXTREMELY TOUGH, and I have been thinking about my vote for this for the past few days. The Town Center of Chester vs the Nature of Washington is a really tough call to make. However, at the end of the day, I decided to give the slight edge to Chester because of the great restaurants that Stylo and WestRiverTraveler were talking about. I haven't been to any, but after doing some research, I feel like the restaurants that Chester has to offer are probably more special than anything in Washington.
Norwalk vs Colchester - This is also not an easy choice for me either. I really do enjoy the town center of Colchester and love how it kind of has that small town / community feeling, but Norwalk is a city with so much character, and there's also Rowayton which is beautiful. Probably my second favorite city of the whole state after New Haven.
Old Lyme vs New Milford - Very Easy pick, and honestly I am surprised by the people that have picked New Milford
Stonington vs Wethersfield - Also a very easy pick. Wethersfield is kind of meh in my opinion, and Stonington is so beautiful.
Darien vs Trumbull - Neither town is my favorite, but both are pretty decent towns. I probably would've picked Trumbull a few years ago, but I am starting to appreciate Darien a little more as a town most recently. It is very upscale, and I could never afford to live there, but it does have some really ritzy and beautiful housing to look at, and the Norton area is great to walk around and look at the houses. Darien is also coastal. I couldn't imagine living in either town, as Darien is way beyond my budget, and Trumbull is just not my kind of town.
Westport vs Southington - 100% Easy Pick
Simsbury vs Easton - Interesting matchup. I feel like Easton is just very rural though and there's a lack of amenities and restaurants. Simsbury also has some rural areas but it has a bit more in closer proximity. Also I love the areas near West Simsbury, and there's Tulmeadow Farms which has great ice cream.
Milford vs Cheshire - Easy Pick
Kent vs Canton - I don't get all the hype for Kent. Canton has a huge variety of outlets and Collinsville.
West Hartford vs Monroe - Easy pick. Monroe is nice, but West Hartford just has so many great restaurants and a lot of amenities. I also enjoy the downtown area and just how a bunch of the restaurants are setup.
Stamford vs East Haddam - The city can be a hit or miss for some people, but I do like the city of Stamford, and the northern part of Stamford is very special as there's a lot more space and it's beautiful. Also growing tech industry.
Madison vs Portland - This is honestly not an easy pick. I really do love the Brownstone Adventure Amusement Park in Portland, but I really cannot take it over Madison. The Surf Club is the BEST beach in the state, and the downtown while small is quite pretty!
Wallingford vs Oxford - Both are great towns, but Wallingford just has more to offer.
Essex vs Groton - Tough one, but Essex wins for me. I do appreciate Groton being coastal and having some great areas, but Essex is just too unique and special not to vote for it. The town center is gorgeous, and you've got the Steam Train and Riverboat which are very essential tourist attractions in the state. I LOVE the steam train a lot.
Wilton vs East Hampton - Much bigger fan of the area that East Hampton is located in along the CT River
Guilford vs New Canaan - Literally one of my favorite towns against one of my least favorite towns in the whole state. Guilford all the way.
Westbrook vs Woodbridge - I don't look at Woodbridge as highly as others do. It's a great town, but I just don't feel it's that special, and Westbrook is coastal.
Ridgefield vs Bridgewater - Beautiful town all around
Greenwich vs Woodbury - Neither town appeals to me that much, but come on Greenwich! Beverly Hills East!
Litchfield vs Brookfield - Easy Pick
Farmington vs Lyme - Probably the underdog here. Honestly Farmington is a cool town, but most Farmington Valley towns just don't do it for me. Simsbury and Canton are probably my favorites of the Farmington Valley, but the rest are just decent but nothing special. Lyme, despite being kind of bare and rural does have a lot of beautiful nature.
Branford vs North Stonington - Easy
Middletown vs Deep River - VERY TOUGH!!! Deep River is prettier, but Middletown is very unique and I do enjoy the downtown and restaurants it has to offer. I also like the way some of the buildings are made. If this was Chester or Essex, I'd probably choose them over Middletown, but I feel like Middletown slightly edges Deep River for me by a hair.
New Haven vs Cromwell - Easy Pick
Salisbury vs Southbury - Tough call, but I believe Salisbury has the highest elevation point in the whole state.
Glastonbury vs New Fairfield - Easy Pick
Newtown vs Clinton - Gotta give Newtown this one. Mainly for Ferris Acres Creamery, LOL. But also Clinton is more of a mediocre town and one of the least desirable coastal towns.
Old Saybrook vs Shelton - 100% Easy Pick
Avon vs Waterford - Probably the slight underdog here, but Avon just does not do it for me. It's another one of those Farmington Valley upscale suburbs that I feel is nothing that special. Waterford has Harkness and is coastal.
East Lyme vs Danbury - I am lost with the votes for Danbury over East Lyme. East Lyme by a mile for me.
Weston vs Bethel - Kind of randomly picked here. Bethel is a bit more affordable.
Losers Bracket:
Manchester vs East Haven - Wish these two didn't have to face each other. Manchester is a very cool city, but I have to pick East Haven as it is coastal and very close proximity to New Haven.
Killingworth vs Windham - Windham is MEH
Enfield vs Wolcott - Don't know much about Enfield, but I am really not a fan of Wolcott at all.
Burlington vs Stafford - Don't know much about either town, but I picked Stafford due to the location.
Marlborough vs Montville - Very pretty town with great woods.
Thomaston vs Bloomfield - To be honest, I mainly picked Thomaston because it's close in name to Thompson, and I really like the town of Thompson, LOL!!!! However, Thomaston has a bit more to offer as well.
Bethlehem vs Lebanon - prettier
Bozrah vs Derby - More so a vote against Derby, rather than for Bozrah
Canaan vs East Hartford - Definitely the underdog, but I do appreciate the town of East Hartford and feel like it is overlooked for being more working class.
Bridgeport vs Lisbon - Mostly for Black Rock Area.
North Haven vs Waterbury - Waterbury is a dump
Newington vs Hartland - Underdog for sure, but Hartland has such a beautiful forest and I love the roads leading up to Massachusetts around that area. Newington is another one of those towns that are just MEH to me.
Mansfield vs Harwinton - UCONN
Brooklyn vs Sterling - Supposedly more agriculture?
Thompson vs Preston - Love Thompson
Rocky Hill vs Torrington - Rocky Hill is one of the better Hartford suburbs and I especially enjoy the Ferry that runs between Rocky Hill and Glastonbury
New Hartford vs Griswold - A bit more forest like I believe
Bolton vs Sprague - Really don't know much about either town besides the location. Just completely randomly picked.
Salem vs Naugatuck - Salem hands down. Naugatuck is one of the worst towns for me, and Salem's got the Salem Valley Farms Ice Cream Shop
Bristol vs East Windsor - Bristol just has a lot to offer. I also like the Carrousel Museum
Cornwall vs Eastford - Better Nature
Ellington vs Windsor - Windsor is mediocre at best
Middlebury vs Meriden - Definitely the underdog here. I feel like Meriden gets overlooked a lot, and I appreciate the city and what it has to offer.
Windsor Locks vs Chaplin - The Airport
Barkhamsted vs Killingly - LOVE the forests of Barkhamsted. Great Nature!
North Branford vs Somers - Some nice agriculture.
North Canaan vs Hamden - Way more to offer
Roxbury vs Beacon Falls - Roxbury is beautiful
Putnam vs Ansonia - Nice main area with a few amenities in the Quiet Corner
Norfolk vs East Granby - Towns are equally decent, but I picked East Granby for the location
Watertown vs Voluntown - Easy Pick
Pomfret vs Suffield - One of the nicest towns of Windham county and the quiet corner
Redding vs Plainfield - Overall the more upscale town
Coventry vs Plymouth - Plymouth is just mediocre
Sherman vs Union - Definitely the underdog, but I do love how Union is the smallest populated town of the whole state. Gotta give it some love. Very rural, and I love it.
Hartford vs Columbia - The Capitol Building and surrounding area is nice!
Woodstock vs Andover - Another really great town in the Quiet Corner. Beautiful
Hebron vs Franklin - Very green and nice woods
Hampton vs Winchester - Hampton is nothing special, but this is more so Anti-Winchester
Morris vs Vernon - Why is this even close? Come on guys, Morris! Vernon is very mediocre.
Orange vs Warren - Nice Town Center and a lot of amenities.
Milford vs Cheshire I know everyone will vote for Milford here. But I feel like of the towns with top school districts Cheshire gets ignored the most. These were actually the two towns our family chose from when we moved in 2020. Milford has the shore and a train station which are two things Cheshire will never have. But it is pretty central to everything, bigger house lots, an awesome school district that is also competitive in many sports. New Cheshire crossing being built now at the 691 exit anchored by Whole Foods. I know it's not a place people go to visit, but it's a great town to raise a family. Some decent eats too, Viron Rondo, Butcher Bro's, Fuoco's, and the owners of Adriana's just sign a 15-year lease to bring a new restaurant to town. Expansion of Bartlem park (where town pool is) is almost done with new turf fields, splash pad, and a great lawn for town events and concerts.
Fairfield vs New London - I love NL but come on. Fairfield = automatic vote
Chester vs Washington - bucking my normal trend of voting coastal/river bc i've spent more time in Washington
Norwalk vs Colchester - nice by the water
Old Lyme vs New Milford - see above. Great fishing!
Stonington vs Wethersfield - see above, on steriods
Darien vs Trumbull - for preserving the island I'll vote for them this year
Westport vs Southington - not even close
Simsbury vs Easton - The more I get to know it I find Easton incredibly special for how rural it is in such an otherwise densly populated area.
Milford vs Cheshire - coastal trend continues
Kent vs Canton - the AT!
West Hartford vs Monroe
Stamford vs East Haddam - dynamic city
Madison vs Portland - another top contender
Wallingford vs Oxford - props to having municipal electricity
Essex vs Groton - sleeper pick. Groton may be the most underrated town in the entire tournament.
Wilton vs East Hampton - has a cute center vs route 7
Guilford vs New Canaan - another finalist pick
Westbrook vs Woodbridge - I'll take the town with the biggest striped bass
Ridgefield vs Bridgewater - closer
Greenwich vs Woodbury
Litchfield vs Brookfield - picturesque downtown
Farmington vs Lyme - Yes, I've been here. Yes, I like the forest.
Branford vs North Stonington
Middletown vs Deep River
New Haven vs Cromwell
Salisbury vs Southbury - most geographically unique town in CT?
Glastonbury vs New Fairfield - sorry Gbury
Newtown vs Clinton - coastal
Old Saybrook vs Shelton
Avon vs Waterford - NL county is so underrated
East Lyme vs Danbury - see above
Weston vs Bethel
Losers Bracket:
Note: This is kind of the wild card round / play in match ups for the Losers Bracket. Haddam, Scotland, Prospect, Willington, Goshen, Durham, Sharon, Granby, Tolland, Colebrook, West Haven, Norwich, Canterbury, Bethany, Middlefield, Ledyard, Plainville, South Windsor, Berlin, New Britain, Seymour, Ashford, and Stratford will start in Round 4.
Manchester vs East Haven - don't like 'staven
Killingworth vs Windham - honorary BGM
Enfield vs Wolcott - one of my most apathetic matchups
Burlington vs Stafford
Marlborough vs Montville
Thomaston vs Bloomfield
Bethlehem vs Lebanon
Bozrah vs Derby - what if I keep voting for it?
Canaan vs East Hartford
Bridgeport vs Lisbon
North Haven vs Waterbury - 0>-
Newington vs Hartland
Mansfield vs Harwinton - it better be in the winners backet again
Brooklyn vs Sterling - ekonk is nice (is this technically in Voluntown?)
Thompson vs Preston
Rocky Hill vs Torrington
New Hartford vs Griswold - I'll take mountains and lakes
Bolton vs Sprague - have to vote for the least famous town
Salem vs Naugatuck
Bristol vs East Windsor
Cornwall vs Eastford - skiing
Ellington vs Windsor
Middlebury vs Meriden
Windsor Locks vs Chaplin
Barkhamsted vs Killingly
North Branford vs Somers
North Canaan vs Hamden
Roxbury vs Beacon Falls - as always, for the route 8 drive
Putnam vs Ansonia
Norfolk vs East Granby
Watertown vs Voluntown - another NL county town underrated
Pomfret vs Suffield
Redding vs Plainfield
Coventry vs Plymouth
Sherman vs Union - mashapaug is gorgeous!
Hartford vs Columbia
Woodstock vs Andover
Hebron vs Franklin - very pretty up route 32
Hampton vs Winchester
Morris vs Vernon
Orange vs Warren
So there we have it. Who is READY to VOTE in Round 3!!!!
Milford vs Cheshire I know everyone will vote for Milford here. But I feel like of the towns with top school districts Cheshire gets ignored the most. These were actually the two towns our family chose from when we moved in 2020. Milford has the shore and a train station which are two things Cheshire will never have. But it is pretty central to everything, bigger house lots, an awesome school district that is also competitive in many sports. New Cheshire crossing being built now at the 691 exit anchored by Whole Foods. I know it's not a place people go to visit, but it's a great town to raise a family. Some decent eats too, Viron Rondo, Butcher Bro's, Fuoco's, and the owners of Adriana's just sign a 15-year lease to bring a new restaurant to town. Expansion of Bartlem park (where town pool is) is almost done with new turf fields, splash pad, and a great lawn for town events and concerts.
I live in Milford, and I totally relate to this. Cheshire is one of nicest towns in New Haven County. It reminds me of Trumbull-- quiet, mostly residential, with great schools.
Milford is awesome-- I can walk to the train and be in NY in 90 minutes. I can be at the beach in 5.
However, Milford has downsides that Cheshire doesn't, and the schools in Milford, while improving, aren't where they need to be.
I live in Milford, and I totally relate to this. Cheshire is one of nicest towns in New Haven County. It reminds me of Trumbull-- quiet, mostly residential, with great schools.
Milford is awesome-- I can walk to the train and be in NY in 90 minutes. I can be at the beach in 5.
However, Milford has downsides that Cheshire doesn't, and the schools in Milford, while improving, aren't where they need to be.
The difference between Cheshire and Milford schools is one or two right answers on an SBAC and one or two less troublemaker/unmotivated students in the school. That's it, maybe they have better hockey and lacrosse nets too. Neither district has kids doing angioplasty, aortic valve stints and other endovascular procedures.
Appropriately so, I'd say. A coastal town as a big QOL booster for many!
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