2018 Best Places to Live in Middlesex CountyAbout this List

Cromwell

• Suburb of Hartford, CT
• 20

Current Resident: Cromwell is such a small, safe and cute little community. The close-knit community provides a friendly atmosphere for everyone!
Read 20 Reviews

• A-

• B+

• 14,021 Population

Essex

• Town in Connecticut
• 19

Current Resident: Essex, a small town on the Connecticut River above the shoreline is full of charm, rich in history (a War of 1812 site - the British burned our ships); with a beautiful views. We've seen rainbows over the River. Downtown celebrates events all year like: the Christmas lantern and boat parade, Halloween bonfire, Burning of the Ships with fife and drum corps, Eagle Watch, Groundhog Day (a big groundhog is costumed and driven down Main Street) and many parades and concerts. We have a 1700's Inn and restaurant, many shops, marinas, the CT River Museum, and sailing clubs. Residents are friendly. Our street holds winter pizza and summer block parties. Although we live in an historic district above downtown, there is wildlife all around. We have turkeys, foxes, 2000+ bird species including herons, osprey, bald eagles etc., raccoons, coyotes, and even black bears! Our Town has good schools, is safe, and peaceful. My brother and I have enjoyed growing up in Essex. We love our town!
Read 19 Reviews

• A-

• A

• 6,588 Population

East Hampton

• Town in Connecticut
• 37

Current Resident: East Hampton is a welcoming community with many different individuals, the community is overall safe with little to no crime. East Hampton is a small town whose school systems are mediocre especially compared to neighboring towns.
Read 37 Reviews

• A-

• B+

• 12,890 Population

Old Saybrook

• Town in Connecticut
• 31

Current Resident: Old Saybrook is the most adorable little coastal town. There are so many beautiful places to drive to, walk, and relax. One thing that Old Saybrook could improve on is more entertainment for younger people!
Read 31 Reviews

• A-

• A-

• 10,162 Population

Middletown

• Town in Connecticut
• 91

Current Resident: Middletown has not only been my home for my entire life but has been an ever changing yet historically rich city nestled right in the middle of Connecticut. Boasting a fabulous Main Street loaded with restaurants, shops, and outings and the home to Wesleyan university this city with a small town feel has something for everyone! My personal favorite part of Middletown though is the people! Middletown despite being a city has a very small town feel where everyone knows each other. I can't go to the grocery store without bumping into at least 3 people I know. Beyond that, Middletown is constantly changing and being renewed by our outstanding public works department and mayor! d
Read 91 Reviews

• A-

• B-

• 46,747 Population

Portland

• Suburb of Hartford, CT
• 35

Current Resident: Great small town experience, but close to major cities. Boston day trips are common. New York is only a short train ride away. Multiple beaches within an hour or so drive. Love the small local businesses in town.
Read 35 Reviews

• A-

• B+

• 5,595 Population

Higganum

• Town in Connecticut
• 4

Current Resident: Being a resident of Higganum my entire life, I have gotten to know this little town fairly well. Although I am viewing it from the eyes of a young adult I still have a pretty good understanding of the town. To begin, there is not much to do. This can be both good and bad. For me, I would prefer to have more options of places to eat and hang out, but some enjoy the more wooded town. The area is very family friendly as the majority of people who live here have kids in the school system or are older and have retired. Generally Higganum is a very safe town. It can get to be exspensive however as taxes are high here. But coming from my viewpoint the people are very nice and the public school systems always perform well.
Read 4 Reviews

• B+

• A-

• 1,708 Population

Westbrook

• Town in Connecticut
• 8

Current Resident: Nothing about this tight-knit community needs changing. With class sizes in the double digits and a large budget for each of the three schools, a student can pave their way through their educational experience with ease. The freedom this town offers within the community's high school baffles me to this day, although; it's perfect for the indecisive students (such as myself) who have a variety of skills and interests and need guidance.
Read 8 Reviews

• B+

• A

• 6,927 Population

Durham

• Town in Connecticut
• 20

Current Resident: In terms of general experience, Durham is a rather nice community to live in. Small town politics and rather high taxes with limited benefits, however, can detract from the overall quality of living. The school system is beyond adequate and students can take their education as far as they are willing to run with it.
Read 20 Reviews

• B+

• B

• 2,777 Population

Clinton

• Town in Connecticut
• 10

Current Resident: I have lived in Clinton since 1972 and have raised my family here. Our local organizations & businesses are very generous, always helping out one another and fundraising for families in need; they also support & sponsor many activities in town. The teachers & schools are extremely supportive. We love our beach and all of its amenities (playground, splash pad, pavilions, & snack shack). Many volunteer youth sports organizations offer several programs for our kids and actively participate in our well-attended parades. Clinton Family Day, the Bluefish 5K Race and Clinton SummerFest are just a few events all families enjoy every summer. The Clinton Park & Rec Dept. offers a wide variety of programs for our youth & adults year-round. The brand new high school facility is very impressive. Community events such as Swoosh for Change, Dodge for a Difference, Dancing with the Stars, Sing-Offs, and Pancake Breakfasts are very popular with residents; proceeds are donated to local charities.
Read 10 Reviews

• B+

• A-

• 13,041 Population

Haddam

• Town in Connecticut
• 17

Current Resident: Lovely little quaint town nestled on the banks of the Connecticut River. It is the only town in the state that is divided by the river and having shores on each side. We are also home to the largest swing bridge in the United States that connects Haddam to East Haddam. We are centrally located and have great access to Route 9 with easy access to both 91 and 95!
Read 17 Reviews

• B+

• A-

• 8,303 Population

Chester

• Town in Connecticut
• 9

Current Resident: Greatest small town in CT! Great New England feel. Very close knit feel with all other residents of the town. Lakes, state forests, and a wonderful downtown area with shops and restaurants.
Read 9 Reviews

• B+

• A

• 4,286 Population

Deep River

• Town in Connecticut
• 11

Current Resident: Deep River is a small but very friendly town. We moved here five years ago nd love it here! Everyone smiles at you and says hello. Excellent schools! Cute downtown. Helpful librarians, good recreation programs. Small town but much to offer. The town has everything to offer including a grocery store, a convience store, pizza shops, restaurants, pharmacy, hardware store, laundromat, bakery, consignment shop, an exercise facility etc. Deep River sits on the Connecticut River. It is als close to route 9 and 95. Central to most everything. There are two outlet malls within ten miles. The city of New Haven is about 45 minutes away as is the Capital city of Hartford. Close proximity to hospitals. The Connecticut Shore line is a short distance away. Highly recommend Deep River, CT.
Read 11 Reviews

• B+

• A

• 4,547 Population

Lake Pocotopaug

• Town in Connecticut

• B+

• B+

• 3,479 Population

Middlefield

• Suburb of Hartford, CT
• 16

Current Resident: I love Middlefield, CT. My family has been in Middlefield for three generations now and we have historical ties with the town. I enjoy the "small town" advantages of living and working here, such as meeting most of the people in town, being greeted by name in local shops, and knowing the back roads throughout the town like the back of my hand. There is a comforting notion of casualty and safety throughout Middlefield, which some people recognize as being for the most part lost throughout Connecticut. The school system, which is regionalized with Durham, is wonderful, the small shops are largely family-owned and also high quality, and the views throughout the town are rewarding.
Read 16 Reviews

• B

• B

• 4,402 Population

East Haddam

• Town in Connecticut
• 24

Current Resident: East Haddam is a wonderful place to live. School system is great, and the teachers are dedicated to the achievements of the students. We also have a great sense of community. Many nature reserves and land trusts for outdoor enthusiast.
Read 24 Reviews

• B

• B+

• 9,072 Population

Saybrook Manor

• Town in Connecticut

• B

• A-

• 1,055 Population

Killingworth

• Town in Connecticut
• 15

Current Resident: Killingworth is a beautiful, growing town with rural charm. The schools are excellent, with low student-to-teacher ratios that you’d generally only find in private school settings. There are miles of public hiking trails and wooded country roads, but you have the added benefit of being only 10 minutes from Long Island Sound beaches (with resident beach rights in Clinton— the best of both worlds!). Home prices are excellent, especially compared with neighboring Madison. And most importantly of all, despite the many beautiful old farmhouses and new builds to choose from, it is a truly down to earth place to live. Worth the extra few minutes on the commute to come home to this small town—a great place to raise a family!
Read 15 Reviews

• B

• A-

• 6,441 Population

Moodus

• Town in Connecticut
• 11

Current Resident: Moodus is a very small town that I have lived my whole life. The community is very close, and you know just about everyone who lives here. I have no complaints about the schools or teachers. The only complaint that is common in Moodus is with it being such a small town it can be hard at times to find entertainment as a teenager/adult.
Read 11 Reviews

• C+

• B+

• 1,076 Population