Flanking Interstate 91’s west side in south-central Connecticut, the Highland neighborhood consists of a series of small subdivisions set within foliage in Middletown. Residential housing began to take root in the past half century or so, superseding the farms that primarily occupied it before. Despite its seeming remoteness, locals are less than 10 miles from Cromwell and Middletown and have access to annual events, which range from Pride celebrations to holiday parades. “Highland is within the city of Middletown,” says Siobhan McLaughlin, a senior sales associate and team leader for the Siobhan McLaughlin Team. “It has a very New England country and rural feel, yet you are part of a small city, which is great because you have all the convenience and activities you would find in a bustling, small city.”
Despite few prominent local businesses and diners in or alongside the neighborhood, the total number of which could be counted on one hand, Highland’s balance comes in the form of its proximity to the larger cities paired with its rural environment. “You feel like you’re in the country, but within a 5-to-10-minute drive, you have everything you need,” McLaughlin, who grew up in the area, says. Interstate 91’s breadth runs northward from Connecticut to the Canadian border, and as such Highland residents aren’t far from taking a trip north to Hartford, Springfield or beyond. “It’s a bucolic country retreat,” McLaughlin says. “There’s historic homes, horse farms and it’s a beautiful area to walk, with some nice vistas. It’s a very beautiful area of town.”
Colonial-style homes are the most common form of architecture in the Highland neighborhood, along with some Cape Cods and ranch-style homes mixed into the landscape. “That part of town runs the gamut,” McLaughlin says. “You have newer constructions, rather large homes that could be over or around $1 million, or mid-century, smaller homes that may be closer to $300,000.” Some properties can even date to the 1700s. “It still has that nice, country feel,” McLaughlin says. “There’s a lot of historic homes.” The area also has a CAP crime score of 1 out of 10, significantly lower than the national rate of 4.
Homes in Highland are spread out, adding to the rural atmosphere, and larger lots are common. “It has a quaintness and New England feel, yet you are smack in the middle of the state and just minutes from every convenience,” McLaughlin says. “It kind of gives you the best of both worlds. It’s a great little area.” Prices usually range between $300,000 and $700,000. “There’s definitely some closer, more densely populated little cul-de-sac developments that were built in the 1980s with the sidewalks,” McLaughlin says, “or you could have a mid-century house that has an acre with a little barn in the back.”
The Red Fox Restaurant sits just off of the east side of Interstate 91, serving as the closest restaurant to Highland’s residential areas. Its menu ranges from seafood and pasta to steaks and a buffet setup, and the establishment also offers catering. Residents often head into Middletown or Cromwell for more options. “Any restaurant you could ever want is along Main Street there,” says Matthew Egan, a broker associate with Regency Real Estate. “There are some really cool tapas places and a really nice vegan restaurant, which is called It’s Only Natural. There’s always awesome dining.” Less than 3 miles north, the Cromwell Diner has stood for more than 30 years and serves classic American fare. Near the diner, Café Fiore offers Italian food to customers.
Shoppers also have to head beyond Highland’s borders. “In Highland proper itself, there’s really no businesses other than the McInerny Flower Shop,” McLaughlin says. “It’s literally the only business in Highland.” The family-owned florist storefront is a local staple. For general needs, there is a Walmart less than 2 miles north in Cromwell, while grocery shoppers head to about five miles east to Market 32 in Middletown. “Growing up here, we tended to do our grocery shopping in the Cromwell area,” McLaughlin says. “The closest grocery shopping is in Cromwell. Cromwell, Berlin and Meriden are very close by. There are a lot of different areas to experience, so it is convenient to all of those as well. In Cromwell, there’s a lot of shopping.”
Lamentation Mountain rises less than 1,000 feet on the west side of Highland, but it is the site of the Alice Fern Bruce Preserve, which spans almost 50 acres and offers trails for visitors. “There’s a lot of activities close by,” McLaughlin says. “The Blue-Blazed Trail goes through part of Highland, so there’s a lot of hiking opportunities.” Doctor Francis Giuffrida Park is less than 5 miles southwest, spanning almost 600 acres and encompassing multiple trails, lookouts at the surrounding landscape and more.
“Lamentation Mountain and Giuffrida Park are the closest recreational areas,” McLaughlin says, “because a lot of Highland is privately-owned.” Hikers can also take to the Highland Pond Preserve, while golfers hit the links at Miner Hills Golf Course across Interstate 91 to the east. Other conservation areas and preserves sit in the surrounding area.
Even in the farthest reaches of Highland, from the subdivisions set within the rural landscape, residents are less than 3 miles from accessing Interstate 91. “That’s the nice thing about it,” McLaughlin says. “Even though you feel like you’re in the country, you can get on major highways.” Via the interstate, New Haven is less than 25 miles south, while Hartford is under 20 miles north. Drivers can reach the Berlin Turnpike, which runs through Hartford and New Haven counties, in less than 5 miles north. “They call it the Berlin Parkway because it goes from New Haven to Hartford, and there’s all sorts of restaurants, shopping and events along that road,” McLaughlin says.
A number of locations in Highland are on the National Register of Historic Places, thanks to their cornerstones dating to several centuries ago. Though Highland doesn’t have many events itself, being a part of Middletown means residents aren’t far from annual gatherings. “Middletown has a ton of events,” McLaughlin says. “Downtown Middletown is a happening place. There’s always something going on and there are tons of festivals.”
Middletown PrideFEST takes place in the early summer each year and is hailed as the biggest Pride celebration in the entire state. “People come from all over,” McLaughlin says. “There’s always so much going on in Downtown Middletown. There are always art shows, craft shows and everything.” Other gatherings include seasonal celebrations and car shows. “They have a holiday stroll every weekend during the holiday time,” McLaughlin says, “and car shows, which totally shut down Main Street."
Residents are close to other area events as well, including holiday celebrations in Westfield to the east. “Westfield has their own Memorial Day parade, and it’s amazing,” McLaughlin says, adding that local scout troops, the fire department and other organizations take part. “Everyone gathers at the fire department afterward to have hot dogs and beer. It’s a very small, community event – it’s very quaint.”
Though there aren’t any schools within the neighborhood itself, Moody Elementary School is located across Interstate 91 to the southeast and serves as a starting point for students in the area. It scores a B-plus with Niche, while Beman Middle School, formerly Woodrow Wilson Middle School, receives a C-plus rating. Middletown High School gets a B from Niche, offering a student-to-teacher ratio of 11 to 1 and campus publications like a yearbook, newspaper and creative arts magazine.
