Ducking into a concrete underpass near Middletown City Hall at 10 o'clock one morning, I intruded on a tipsy fellow answering the call of nature. Averting my eyes, I hurried through the tunnel beneath a four-lane highway and came out at a narrow riverfront park. A couple in heavy coats huddled on a bench in the raw wind. A discarded wine bottle in a paper bag lay by the railing alongside the deserted Connecticut River.
The river made Middletown's fortune in centuries past. Busy docks shipped lumber and livestock to ports along the East Coast and the Caribbean. Sail turned to steam and ferries continued to move passengers and cargo up, down, and across the river, until rails and roads linked the country. Route 9 was built along the water in the 1950s, cutting off the town from its strongest commercial justification, the river.
But there's still good reason to visit Middletown. Each fall, 2,700 students arrive to work toward a liberal arts education at Wesleyan University, five blocks from Main Street.
One long weekend recently, my college roommate and I drove our teenage daughters to several ''reach" schools in Connecticut. After a tour and information session at Wesleyan, we explored the town attached to the gown.
''Fifteen years ago, like so many other small towns, Main Street was closed-up shops, empty storefronts," said Dione Longley, Middlesex County Historical Society director. ''I wasn't sure you could ever get Middletown back."
However, city officials joined the National Trust for Historic Preservation's Main Street Program to revitalize the area. Now, Longley said, ''It's one of the few places where you can go to dinner and see a movie and not have to get in a car and drive."
Main Street is lined with handsome historic buildings that have been restored and repurposed. Longley's office is in the General Mansfield House, home of the Union general who died at the Civil War Battle of Antietam. Joseph Mansfield married the girl next door and moved into her father's Federal brick mansion. That romantic story appears on a historic marker, part of the Middletown Heritage Trail.
Main Street is as wide as a runway, so Middletown doesn't have the intimate charm of some small-town shopping districts. I had to hustle 28 paces to cross the street before the light changed. It felt as if I should be looking out for airplanes, not cars.
While the girls tried on skimpy tops at Bob's Stores, we found hardware, Heath Bar ice cream, and Haitian art in a span of eight blocks. For entertainment, there's a roller skating rink and a new 12-screen multiplex.
Tech-savvy town leaders offer free Wi-Fi access all along Main Street. Still, Middletown hasn't changed all that much over the years, said Bill Sibona, owner of Central News.
''It's a little city," he said, ''but it's still a small town."
The bright red ''Cigar" sign in the window announces that Sibona sells more than newspapers and magazines. The aroma of aged tobacco permeates the storefront. Display cases hold 30 to 40 brands of cigars in colorful boxes, the kind children used to keep their treasures in. Sibona imports most of the cigars from Honduras and the Dominican Republic, but, he said, ''Most of them have the Connecticut-shade wrapper."
''Wait a minute," I interrupted. ''Connecticut tobacco?"
Sibona explained that tobacco grown in Connecticut under canopies produces a thinly-veined leaf perfect for wrapping cigars. ''It's the best tobacco in the world," he said. A smile widened his walrus mustache as he recalled, ''When we were kids, there were tobacco fields all over the place. All the kids worked tobacco."
Next to Central news is Middlesex Fruitery, a gourmet grocery where, Longley said, Middletown's movers and shakers tend to congregate. Everything is discussed while squeezing the melons.
We dined on Main Street at the best vegetarian restaurant in the state, according to a Connecticut Magazine poll. Supporting columns tied with funky 1950s aprons epitomize the whimsical style of It's Only Natural. Chef/owner Mark Shadle's classic culinary training is reflected in the menu, including tempeh ''crabcakes" and vegan chocolate hazelnut cake.
Driving west of town, uphill away from the river, took us past a sprawl of fast-food joints and strip malls to a budget motel for the night. ''No parties" warned a hand-lettered sign on the bullet-proof glass protecting the desk clerk. The next day, we waited in line outside O'Rourke's Diner on Main Street for breakfast before our half-hour drive south to New Haven, home of Yale University.
With 123,000 people, New Haven is three times the size of Middletown, but faces similar challenges. Interstate 95 long ago cut off the city from Long Island Sound, and it is digging its way out of an economic slump. Plus, it has had to contend with an outdated bad reputation.
Scott Healy, executive director of the Town Green Special Services District, said, ''Some people were so inclined to dismiss New Haven that if they saw a gum wrapper on the ground, it just confirmed every fear they had of the city." The business improvement district was formed in 1996 to change the reality -- and people's minds -- by sprucing up downtown and putting friendly guides on the streets.
Instead of reviving a walkable Main Street, New Haven is promoting its creative economy.
''We don't have to be ye olde New England pristine, quaint town," said Healy. ''We have a little bit more edginess to us. And I can't emphasize enough the vibrant art scene that represents all sorts of visual, performing, musical, and dramatic arts."
Frank Bruckmann is a painter who came to New Haven and stayed because of the thriving arts community.
''We all know that once artists move in and make a place funky and cool, it becomes more desirable to everyone," Bruckmann said.
The results are in the shops and restaurants of Westville, where he lives, and the lofts of Ninth Square, a former warehouse district south of historic New Haven Green.
After a Yale tour guide walked us through the campus and the history of the university, we wandered the Broadway shopping district. A dazzling sidewalk display of fresh flowers drew us into Gourmet Heaven to choose lunch from steaming buffet tables and cold deli cases stocked with salads, meat, and cheese.
Up the street, pastel-colored beaded necklaces, bracelets, and earrings draped the walls and tables at Alexia Crawford. I snagged a photo album encrusted with pink seed beads for my daughter at
Abandoning the girls at a coffee shop where the tables were crowded with lattes and laptops, we moms checked into the Farnam Guest House on prosperous Prospect Street. The owners were out, so we let ourselves in with a key left for us under the welcome mat. We made tea and unwound in the large Wedgwood-blue parlor furnished with a grand piano, a pump organ, plants, books, and a ceremonial sword displayed over the door.
Downtown New Haven offers 123 restaurants. We picked an Eritrean spot on the principle that when dining out, eat what you can't get at home.
Owner Gideon Gebreyesus welcomed us to Caffé Adulis across from the Shubert Theater on College Street. Our dinners arrived on a metal platter two feet wide. Various stews were arranged on crepe-like sourdough flatbreads. More flatbread -- plain, beet, and carrot-flavored -- served in lieu of cutlery. We dug in with our fingers and savored the unfamiliar spices. Later, sated, we nested under goose down in a huge second-floor room at the B&B.
On an early morning run, my friend discovered 425-acre East Rock Park along the Mill River, with its a rose garden, hiking trails, tennis courts, and a road to the Soldiers and Sailors Monument on the 380-foot summit.
Black bean soup is the specialty at the Atticus Bookstore and Cafe on Chapel Street, but not for breakfast. We chose eggy striatta, chocolate croissants, and an informal seminar on New Haven's modern architecture from Edward De Barbieri, a Yale divinity student sitting at a nearby table. The steel and glass building we sat in houses the Yale Center for British Art. It was architect Louis I. Kahn's last project, completed after his death in 1974, and was the first US museum to incorporate retail space in its design. Kahn's first big commission, the Yale University Art Gallery (1953), is across the street.
New Haven Coliseum, built in 1972, is in the midst of demolition; the area will be the site of the new Long Wharf Theatre, possible hotel and residential development, and a new junior college.
''Jim Morrison was arrested there, if you know the song," DeBarbieri said, referring to the line ''Blood in the streets in the town of New Haven" from The Doors' song ''Peace Frog."
The streets in New Haven were empty that morning. Whoever wasn't in church was shopping at Ikea. The Swedish home furnishings retailer opened its first outpost in New England here in summer 2004. Healy said the blue and yellow big box by the harbor brings more than 12,000 people a day to the city.
So, you certainly need not know a Yalie to enjoy New Haven.
Contact Marcy Barack, a freelance writer in Maine, at email@example.com.