20 Great Places to Retire

When the time comes, you'll know it. But you may not know where to spend it. Here are some suggestions.You may have far-flung plans for your retirement, or you may plan on staying right where you are. But for a growing number of aging baby boomers in Connecticut, the plan is to get out of the house they're in and into a smaller place in a pleasant location not too far from family and friends. That's why during the last 10 years or so there's been an explosion of new housing, and even new communities, for "active adults" over the age of 55 in the state.

With such a huge trend staring us in the face, we decided to get on board with a look at some of the top retirement towns in Connecticut. This is not a scientific survey, but in most cases it does take into account things like cultural amenities, public safety, proximity to medical centers and the availability of appropriate housing. In the range of towns we've selected, we've tried to find something for everyone. But at the same time, we understand that it's possible to experience a perfectly enjoyable retirement in any of the state's 169 towns. Ultimately, it all depends on you, your situation, and your likes and dislikes.

For those who might be looking, however, here are some places to consider.

Shoreline Twins: Madison & Guilford

It wouldn't be hard to make a case for any of Connecticut's 24 shoreline towns as a good place for retirement, but Madison and Guilford stand out for several reasons. First of all, they are both far enough east along the shore so that both I-95 and Route 1 aren't hellishly crowded with traffic at all hours of the day and night. Second, both enjoy attractive, walkable downtown shopping/civic/entertainment districts, with Guilford's clustered around the town green and Madison's along the Post Road. The third advantage is ready access to Long Island Sound. Madison is home to 936-acre Hammonasset Beach State Park; it can get hectic and crowded on hot summer days, especially on weekends, but the rest of the year it offers the state's longest beach and miles of seaside hiking trails. Guilford's waterfront offerings are more modest, but the local Chaffinch Island Park is one of Connecticut's best picnic spots. Finally, both towns are already senior-friendly, with suitable housing, strong libraries and a number of active organizations for seniors. Emergency and many other medical needs can be taken care of at the Yale-New Haven Shoreline Medical Center in Guilford.

Urban Allure: New Haven

For some retirees, this is an irresistible package: restaurants of every cuisine and price, live music and theater, art and history museums, lectures and sports events-and all within walking distance or an easy ride via public transportation. Such are the many charms of New Haven, which in recent years has proven to be a desirable destination for bored empty-nesters willing to ignore the city's troubling crime rate as they trade the big house in the suburbs for a city apartment, condo or loft. The key to New Haven's allure is Yale University, of course, with its ambitions, traditions, intellectual fervor and youthful vigor spinning off everything from dinosaur displays and architectural treasures to cabaret acts and all-night falafel joints. But there's more to New Haven than that-there's Southern Connecticut State University and Albertus Magnus College, two major hospitals, a working harbor and easy rail access via Amtrak and Metro-North. And then there's the pizza, which we're happy to rate as the best in the world until someone can prove otherwise. The housing opportunities are varied, but tend to get more interesting (and expensive) the closer you get to the Yale campus.

20 Great Places to Retire

When the time comes, you'll know it. But you may not know where to spend it. Here are some suggestions.

• • •

Husky Heaven: Mansfield

It has taken an uncommonly long time for Mansfield, and especially its southern outrider, Storrs, to catch up with the fact that an enormous state university has been growing in their midst. Even as the state poured billions of dollars into UConn's infrastructure in recent years, the surrounding area seemed stubbornly to resist becoming a "college town" by providing cafes, shops and other amenities that might be enjoyed by students, their parents, alumni and university faculty and staff. But now all that seems to be changing with the plans for Storrs Center, to be built on a 50-acre parcel near the campus. According to a press release, "The town plan will knit architecture, pedestrian-oriented streets, small lanes and public spaces into a series of neighborhoods." The plan also calls for retail, restaurants, office space, several types of housing (including apartments and condos above the shops) and plenty of open space. Combined with UConn's existing facilities-Jorgensen Center for the Performing Arts, William Benton Museum of Art, Gampel Pavilion, etc.-Storrs and Mansfield suddenly look more attractive to retirees yearning for an affordable college town, especially if it was their own. Everything is planned to be in place by 2014.

Golf Course Factor: Danbury

All other things being equal, sometimes it's nice to retire to a town with a superior municipal golf course so you can take advantage of those carefree weekday mornings and favorable greens fees. Danbury is one such place, with an ample array of condos on the market (over 1,200 were sold in 2006 and 2007) and houses at reasonable prices, at least for Fairfield County. More to the point, Danbury's Richter Park Golf Course has been rated one of the top 25 municipal courses in America. As a Danbury resident and a senior over 62, you can get a weekday round for $27 compared with $85 for a nonresident. A season pass for 50 rounds at $1,000 compares very nicely with the outsider's rate of $2,750. And speaking of becoming a resident, of special note in Danbury these days is an enormous new housing complex called Rivington being built on the sprawling former campus of Union Carbide; among its offerings are new mid-rise condos and townhouses in a 55-plus "village" called Rivington Encore. (Golfers will also find a lot to like in Bloomfield, just north of Hartford, where the superior municipal course, Wintonbury Hills, offers great deals for resident seniors. The town is also home to several well-regarded senior communities, including Duncaster and Seabury.)

County Seat: Litchfield

Here is the heart of Litchfield County, established on high land along what would become the busy Hartford-Albany Turnpike, and once, in early post-Colonial days, the third most populous town in the state. Today, Litchfield offers small-town pleasures that run from the simple to the sophisticated-and enough of them so you won't feel you're stuck in Smallville. To begin with, Litchfield's architecture is some of the most interesting in Connecticut. Its 19th-century mansions line North and South streets like great ocean liners waiting to go out to sea, while the white-steepled Congregational Church on the green is perhaps the most photographed in the state. Elsewhere around the green, there are stylish shops, several types of restaurants, and convivial watering holes where, on occasion, the town's remarkable camaraderie and joie de vivre can be glimpsed. The outdoors plays into Litchfield's allure as well. Without leaving town, you can climb to the observation tower atop Mount Tom, sail on Bantam Lake (the largest natural lake in the state), cross-country ski through Topsmead State Forest or hike mile after mile in White's Woods, part of the 4,000-acre White Memorial Foundation. You'll be happy to learn that not all the houses are the size of ocean liners, and that some of the smaller ones within walking range of the green are quite reasonably priced.

New York State of Mind: New Canaan

One of the tricks of enjoying a comfortable retirement in lower Fairfield County is finding a place that's not too close to the noise, pollution and aggravation of the I-95 corridor but that's at the same time within shouting distance of a commuter rail station, and thus connected to all the pleasures of Manhattan. Another trick is to have a lot of money. If you qualify on both counts-and are conversant on the subjects of arbitrage and Republican fund raising-New Canaan may be just the place for you. This classic New York suburb is well-known for its multimillion-dollar single-family homes, but it also saw sales of 113 condos during the past two years, with a median sales price of about $625,000. Even if you never venture in to the big city, however, there's plenty to like in New Canaan's prosperous little town center, where a nice variety of shops and restaurants beckons. Another asset here is the nature of the retirees who already live in town, and who have lived here for years-they are largely affluent and well educated, and they make sure the local civic organizations and cultural institutions are well financed and intelligently run. As you may be aware, this is not the case in every Connecticut city and town.

Bend in the River: Middletown

How about a well-located college town with extensive river views and lots of condos selling at a median price of about $150,000? Now that I have your attention, let's talk about Middletown, where the Connecticut River takes a sharp turn east and heads down to the Sound. Middletown is the home of Wesleyan University, whose 3,000 or so very independent-minded undergrads and graduate students do their best to keep things interesting for the townsfolk. The school occupies 360 acres right in the center of town and generates satellite bookstores, shops and restaurants, as well as its own museum, galleries, theater, lectures and sports events. If your interests lie a little farther afield, Middletown is located midway between Hartford and the shore, and is an easy drive to either, and is also minutes away from good public golf courses in neighboring Middlefield and Portland. What's especially nice about Middletown are its house prices. A cool two-bedroom, two-and-a-half-bath condo in Parker House, a refurbished mill near the Wesleyan campus, recently went on the market for $219,000. A brand-new detached condo in Middletown's Bartlett Hollow starts at just under $330,000.

20 Great Places to Retire

When the time comes, you'll know it. But you may not know where to spend it. Here are some suggestions.

• • •

It's all Going On: West Hartford

What ever happened to Hartford's downtown? Well, young postgrads are said to be settling there, but for retirement-age people it seems to have moved five miles west, to the center of West Hartford. Here, where Main Street and Farmington Avenue meet, this exemplary inner-ring suburb has reinvented itself in recent years with a colorful array of shops, restaurants, amusements and even a brand-new, 20-acre multipurpose commercial/residential development called Blue Back Square. The result is a destination for retirees who want to feel like they're in the middle of things, with lots going on right outside their door and more, such as theater, concerts and sports events, taking place next door in Hartford. West Hartford Center has long been a shopping destination, but now, with 140 shops and restaurants, it's one of the most vibrant in the state. Blue Back Square alone includes a Crate & Barrel, Ann Taylor, REI, Whole Foods, Barnes & Noble and Criterion Cinemas. The housing in this part of town is varied and interesting too, with classic apartment buildings mixing with some newer condos. The prices probably aren't high enough to send you into shock, either. If you've been searching for an active retirement with an urban feel in a very walkable milieu, this may be the place.

Life in the Village: Stonington

If you are one of those who feels the pull of the sea, you may also respond to the magnetic charms of Stonington Village. Here, in the extreme southeastern corner of Connecticut, on a mile-long point of land extending south from Stonington proper, you can smell the salt water wherever you go and see it just about wherever you look. It's a place where Connecticut's maritime history lives on and where the sense of being near open water informs the local commerce, the architecture and the way of life. There is also an intense feeling of community in Stonington Village (read In the Village by Anthony Bailey for background), with friendly greetings the norm as residents stroll up and down the narrow lanes to shops and restaurants. There aren't many homes for sale at any given time in this confined space (although a handful of water-view condos hit the market recently), but the rest of Stonington has much to offer, too, not only along the shore in Mystic, Lord's Point and Pawcatuck, but also behind stone walls in the rolling backcountry. At certain times and in certain places, Stonington can feel quite a bit like Martha's Vineyard-without the ferry ride.

Deep Country: Woodstock

Here's the Connecticut not many of us are familiar with, way up in the northeast corner-the Quiet Corner-bordering Massachusetts and only a few miles from Rhode Island. The pleasures of life in Woodstock are pretty much what you make them, but in one way or another they're bound to be played out against a backdrop of fields and working farms. Woodstock's 60.5 square miles (it's the second largest town in Connecticut after New Milford) are home to 45 farms, including 12 family-owned dairy farms, the most of any town in the state. The "Woodstock Grown" section of the town's Web site shows that local farmers also produce hay, honey, Christmas trees, maple syrup, wine and many varieties of fruits and vegetables. Housing prices in Woodstock also reflect the rural nature of the place. There are condos for sale (45 sold over the last two years), but rarely do they go for more than $200,000 (a fixer-upper end unit right by Roseland Park's nine-hole golf course was recently on the market for $109,000). Or maybe it's a cottage or smallish house you'd prefer on or near one of Woodstock's many lakes. A new two-bedroom, two-bath, 1,500-square-foot Cape with rights to Lake Bungee goes for $225,000, while something right on the lake goes for a little more. The crickets come at no extra charge.

Just About Perfect: Ridgefield

There is no town in Connecticut that's completely free of crime, of course, but Ridgefield comes amazingly close. According to statistics kept by State Police, over the past three years Ridgefield's crime rate has been 0.55 major crimes per 1,000 residents, the only rate below 1.0 in Connecticut. For amusement's sake you may wish to compare Ridgefield's crime rate with that of Fairfield County roommates Westport (4.05), Redding (6.49) or Bridgeport (28.60). In fact, Ridgefield's real major crime is that more people can't afford to live here. The town's virtues go well beyond public safety, too. There's a vibrant, walkable downtown, notable museums and an active theater and concert scene, mostly at the Ridgefield Playhouse for Movies and the Performing Arts. There are restaurants of all sorts, a 300-acre state park and a good public golf course. There's rail service to New York via the Danbury spur and even a reasonably active, if expensive, market in condominiums, with 52 sold in 2007 at a median price of $628,000. But who are we to put a price on living in Connecticut's storybook suburban town?

Ocean Breezes: East Lyme

Want to head to a milder climate for your retirement? Try the Connecticut coast. The average high and low temperatures in January are 33 and 14 in Torrington, up in Litchfield County, but 38 and 24 in East Lyme; in October, it's 60 and 37 in Torrington, and 63 and 48 in East Lyme. In addition, it snows on average about 50 inches in the Northwest Hills and only 30 inches in East Lyme. But let's not talk about snow! Let's talk summer instead, when the cool salt air wafts in from the Sound, or fall, when strolls along the town's mile-long boardwalk or the beach at Rocky Neck State Park are local pastimes.  The center of things in East Lyme is Niantic, located on the bay and in many respects still charming as an old maritime village. You can shop and dine in Niantic, and live here, too, most notably in a new development called 38 Hope Street, where 150 one- and two-bedroom apartments and townhouses will take shape this summer within easy walking distance of town and the waterfront. Overall, East Lyme is one of those Connecticut shore towns that seems particularly welcoming to the active-adult crowd; in the last two years, 182 condominiums have sold at a median price of  about $238,000.

20 Great Places to Retire

When the time comes, you'll know it. But you may not know where to spend it. Here are some suggestions.

• • •

Price & Promise: Naugatuck

This entry requires a leap of faith and perhaps a change in preconceptions. Naugatuck is a gritty old manufacturing town on the banks of the Naugatuck River just south of Waterbury-and was once the place where everything from Keds to Mounds bars were made. Following a long postindustrial decline, the borough in recent years has found some favor as a bedroom community for the ever-expanding swarms of people who work in Fairfield County but can't afford to live there. They like Naugatuck's cost of living (median condo price: $139,000) and the easy ride up and down Route 8 (except for the damnable Commodore Hull Bridge in Derby/Shelton). But now something new and quite unexpected is in the works. If all goes as planned-and things were moving right along in early spring-a $707 million live/work/play project known as Renaissance Place is going to take advantage of Naugatuck's river frontage and handsome green by constructing a town within a town-1,800 residential units, 500,000 square feet of retail space, 76,000 square feet of office space, a hotel and more on 60 acres. The community (naugatuckrenaissanceplace.com) will be public transit-oriented and independent of national or regional power grids-in short, everything a conscientious boomer is looking for. A happy retirement on the banks of the Naugatuck River? It just might be in the cards.

Beside the Tidal River: Essex

Here's a Connecticut town with an actual pedigree. In a 1996 book by Norm Crampton called The 100 Best Small Towns in America, Essex was deemed the very best of all-and it has wisely used "Best Small Town in America" as a rallying cry ever since. In addition, Essex was recently one of only four Connecticut destinations (along with Mystic Seaport, Mark Twain House and Litchfield Hills/Mayflower Inn) to make it into the best-selling 1,000 Places to See Before You Die. Why all the fuss over this old seafaring town in the lower Connecticut River Valley? Well, Crampton's ranking methods are a little murky, but there's the lovely location on the river, of course, at the very center of what the Nature Conservancy has termed "one of the last great places." And there's the sense of history, evidenced in places such as the Connecticut River Museum and the Griswold Inn, a lively local tavern that claims to be the oldest in the state. Which brings to mind other good spots to eat and drink, and the local playhouse, the galleries and shops, and even, just in case, Middlesex Hospital's Shoreline Medical Center. Active-adult housing is not quite as readily available here as in nearby towns, and what there is tends to be fairly pricey. But isn't that what you'd expect from the "best small town in America"?

Historic Valley Towns: Farmington & Woodbury

Those with a strong sense of history might feel at home in these two well-bred towns, where the very early settlers of Connecticut found sustenance in the riverine soil and enveloping hills. Farmington is easily the larger of the two-an old-line, affluent suburb of Hartford with well-established neighborhoods, good public golf courses, the UConn Health Center, Hill-Stead Museum, many shopping and dining options-and, to be fair, daily traffic adventures on Routes 4 and 10. Farmington has also become a hotbed of condo living for active seniors, with 520 sales over the past two years at a median price of $205,000. Woodbury, located in the Pom-peraug River Valley, offers a far more rural retirement option. Main Street (Route 6) is lined with historic houses, churches and antiques shops. There are also more restaurants here (Good News Cafe, John's Café, Carmen Anthony Fishhouse, Charcoal Chef, Curtis House, etc.) than in any comparably sized town in the state, with the possible exception of Old Saybrook. Add that to the flavor of the Litchfield Hills and Colonial history and you've got an increasingly popular retirement destination.

Lake & Hillside: New Milford

New Milford is home to a nice combination of features for those who might be in the market for a bit of the country life. It's got lots of lakefront acreage on Candlewood Lake (Connecticut's largest), for instance, which gets very busy in summer but is peaceful and lovely the rest of the year. Its large geographic size means there are many back roads and quiet rural retreats offering pleasant views of nearby green pastures, hills and valleys. The Housatonic River runs for miles right down the middle of the town, providing a habitat for fish and game and recreational opportunities for the rest of us. And the town green is one of the most pleasant in the state, surrounded by churches, municipal buildings and businesses. Finally, New Milford is clearly more open than are adjacent towns to the sort of housing that freshly minted retirees are looking for. While neighboring Kent saw sales of only 18 condominiums over the past two years and Washington 10, Bridgewater 3 and Sherman just 1, New Milford had condo sales of 318 at a median price of about $180,000. A wider variety of places where you don't have to mow your own lawn? Now that's a good thing.

Well-Heeled Peace & Quiet: Roxbury & Lyme

When some people think of retirement, they don't see condos or a gated community; they see a sturdy, smallish house, preferably of an older vintage, down a quiet country lane, perhaps with a studio or potting shed attached. They're not looking for organized activities involving shuttle buses and attendance sheets, but rather wish to be left alone to do exactly what they want at precisely their own pace. There are any number of towns in Connecticut where this is possible, but two of the best are Roxbury and Lyme. For one thing, neither town has any condominiums at all, and barely any commercial activity. Roxbury is an uncrowded old farming town that for years has famously served as a retreat for writers (Arthur Miller and William Styron lived and worked here; A.R. Gurney live here now). Most of the farms have by now been turned over to the local land trust, but the smell of hay in the fields remains an intoxicating presence. Lyme, located along the lower eastern banks of the Connecticut River, attracts a saltier crowd, including sailors who put in at lovely, unspoiled Hamburg Cove. A word of warning: Quiet days and nights come at a price-houses in both Roxbury and Lyme are considerably more expensive than the state average.

(This article was originally published on a different platform. Some formatting changes may have occurred.)

This article appeared in the May 2008 issue of Connecticut Magazine

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