2021 Best Places to Live in Middlesex County

Cromwell

• Suburb of Hartford, CT
• Rating 3.88 out of 5  25 reviews

Current Resident: Cromwell has a small town feel but it is very convenient to most places in Connecticut via I-91 and Route 9. For a community of under 14,000, we have a lot available to us right in town regarding shopping and dining options. There is a good mix of big box retail/grocery stores, chain restaurants, and mom and pop stores/restaurants. It's a great town for young families and first time home buyers with a good sense of community. Our kids are not school-aged yet, but I've heard great things about the district and quite a few kids live in our neighborhood; we probably had close to 100 trick-or-treaters last Halloween...Read 25 Reviews

• grade A

• grade B+

• 13,910 Population

Higganum

Current Resident: Small historic town near Haddam Meadows, 7 Falls State Park, Goodspeed Opera House, Higganum Resevoir, Pratt and Whitney shopping and schools.Read 9 Reviews

• grade A

• grade A minus

• 1,285 Population

Old Saybrook

Current Resident: Small coastal town with all the great things! Just enough stores to keep you local and perfect approximation to anything else you will ever need. The people are friendly and very welcoming!Read 36 Reviews

• grade A minus

• grade A minus

• 10,090 Population

Essex

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 28 Reviews

• grade A minus

• grade A minus

• 6,604 Population

Killingworth

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 19 Reviews

• grade A minus

• grade A minus

• 6,392 Population

Middletown

• Town in Connecticut
• Rating 3.81 out of 5  117 reviews

Current Resident: After moving from California to Middletown,CT it was huge leap of faith. I was unsure how I would finish my senior year away from friends and family. However, Middletown kept me busy. I met friends the first week I moved, and the first thing we did was head to main street. From the busy streets of Middletown I was able to come home to a quiet and safe area in my suburban neighborhood. I can't describe how much I enjoyed the move. The scenery, community, just everything is so different and new. I love it...Read 117 Reviews

• grade A minus

• grade B

• 46,511 Population

Haddam

Current Resident: It has a very quaint, small town feel to it. There are a variety of local restaurants to choose from. It is only 15 minutes away from Middletown. In Haddam, there are various hiking trails and parks if you are looking for a fun outdoor place to go...Read 20 Reviews

• grade A minus

• grade A minus

• 8,227 Population

Deep River

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 16 Reviews

• grade B+

• grade A minus

• 4,480 Population

Clinton

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 12 Reviews

• grade B+

• grade B

• 12,944 Population

Westbrook

Current Resident: If you held out a map of Connecticut, focused on the shoreline and attempted to find the town of Westbrook, it would quietly hide in plain sight. As a minuscule shoreline town, it can be relieving to use size as an excuse. Class sizes range from twenty students down to a mere five or six at times and our sport team rosters never spill over thirty names. These numbers serve as reassurance and explain why Westbrook is undeserving of its own “dot on the map.” But why should this be the case? It shouldn’t. In fact, our handful of state titles and first place trophies should serve as motivation for the future, not a despairing reflection of the past. Surrounded by the same fifty-two classmates for eighteen years allowed me to recognize the beauty of a small town. The overused, exhausted reasoning I grew accustomed to hearing my whole life has impacted me in the best of ways. My post-secondary plans eagerly await, originating from the fact that I want more than what Westbrook gave me...Read 10 Reviews

• grade B+

• grade A minus

• 6,903 Population

Portland

• Suburb of Hartford, CT
• Rating 3.87 out of 5  38 reviews

Former Resident: I was born in the neighboring town of Middletown but lived in Portland. I wouldn’t of had it any other way, so safe so pleasant and just a quaint small town with it’s beautiful people. Absolutely looking forward in going back home. Best place ever...Read 38 Reviews

• grade B+

• grade B+

• 5,552 Population

East Haddam

• Town in Connecticut
• Rating 3.73 out of 5  30 reviews

Current Resident: East Haddam is a smaller town with excellent schools. You can find houses next to others, or in the middle of the woods if you so please. I wish more activities were closer, ex shopping/restaurants. There are around 9,000 residents, but the town itself takes up a lot of space. There are lots of trees and wildlife. It's in New England, so of course you get your beautiful snowy winters and warm, sunny summers. East Haddam is on the Connecticut River and has a beautiful swing bridge and Goodspeed Opera House. In the summers, stop by for a Music on the River session in the lawn next to the opera house. You may see planes land in the Goodspeed Airport, or boats dock at the docks...Read 30 Reviews

• grade B+

• grade B

• 9,007 Population

Middlefield

• Suburb of Hartford, CT
• Rating 3.88 out of 5  16 reviews

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

• grade B+

• grade B+

• 4,381 Population

East Hampton

• Town in Connecticut
• Rating 3.67 out of 5  45 reviews

Current Resident: What I love about living in East Hampton is Lake Pocotopaug. In the summertime, there is no rival for water sports in my eye. 500 acres of idyllic fun, with things like water skiing, sailing, swimming, parades, fine dining, and fireworks, it is a lake like no other. With fantastic public schools, it is the perfect place to raise a family. East Hampton Students graduate in large numbers every year.. The one thing that could even be considered a downside is that there is little for night-owls or partiers in town, everything closes up right around 9pm, excluding the lakeside restaurant Angelico's, which is what brings the nightlife score up to average. Also, there is little in the ways of large companies looking for workers, since the town is mostly residential zoned, with little business opportunity from outside towns. But since the commute to larger nearby towns is short, this is not really a problem. Overall, I love living here, and I know that anyone else will tell you the same!...Read 45 Reviews

• grade B+

• grade B

• 12,827 Population

Durham

Current Resident: I really enjoy the town of Durham CT that I live in because most things you need in town are within walking distance. These can include a park, schools (depending on where in Durham you live), gas stations, and a library...Read 24 Reviews

• grade B

• grade B+

• 2,752 Population

Chester

Current Resident: Quaint artsy New England town. Great place to raise a family. Amazing school system!Great restaurants and local shopping.Read 11 Reviews

• grade B

• grade A

• 4,234 Population

Lake Pocotopaug

• Town in Connecticut

• grade B

• grade B

• 3,117 Population

Moodus

• Town in Connecticut
• Rating 3.46 out of 5  13 reviews

Current Resident: It is a small rural town in central CT with lots of back roads and not a single stoplight in town. If small towns are your thing, Moodus is great for you, it takes at least 20 minutes to reach a larger grocery store, and longer to shop at a department store. The people are nice, but it is very politically split which can lead to unrest. It's not exactly a "fun" place to grow up as a teenager because there is nothing to do, but it's safe. It also has great hiking trails...Read 13 Reviews

• grade B minus

• grade B

• 1,391 Population

Saybrook Manor

• grade B+

• grade A minus

• 933 Population