Most Romantic Main Streets



What do Main Streets have that the malls don’t? Atmosphere… History… Romance. They’re the place to go for unique experiences. Candle-lit restaurants, unique wedding destinations, charming streets for strolls, intimate wine-tasting rooms, quaint B&Bs, special historic spots — these are just a few of the things that make Main Street districts a romantic destination. This year, we scoured the nation to find the Most Romantic Main Streets. Here is what we found.

Middletown CT RestaurantMiddletown, Connecticut. Middletown’s allure includes an artful Main Street brimming with elegant restaurants, an award-winning local chocolatier, and the romantic Inn at Middletown, offering the best of New England charm.

  • Dream Date: With its views of Main Street's church steeples and the winding Connecticut River, the Inn at Middletown is the perfect base for a romantic New England weekend. Make a leisurely start with brunch at the classic O'Rourke's Diner, where the culinary talents of Brian O'Rourke have been celebrated by foodies from Gourmet Magazine to The Food Network. Stroll along Main Street, and visit the vintage model train display at Amato's Toy & Hobby, then stock up on regional treats at the New England Emporium. Malloves Jewelers just might give your sweetie some good ideas! Venture past the historic houses on tree-lined College Street to the prestigious Wesleyan University. Take in an eclectic and interesting lecture, a hockey game, or go stargazing at the college observatory. Back on Main Street, your hardest chore will be choosing where to eat. With dozens of choices in just a few blocks, you'll be tempted by Mexican, Thai, Vietnamese, Japanese, and American restaurants, as well as the locavore,organic cuisine at It's Only Natural. But for romance, try Esca's extensive wine list and delicious Italian entrees —deemed “worth getting a babysitter” for by local critics. After dinner, sample the artisanal confections at Tschudin Chocolates and a perfect espresso at Klekolo World Coffee. End your evening with a visit to Eli Cannon's Tap Room for the best variety of local beers and friendly atmosphere, or retreat to the Inn at Middletown for a martini in front of the fireplace at the Tavern at the Armory.

Madison Indiana CarriageMadison, Indiana. You’ll fall in love with Madison’s natural and historic treasures, including lush vineyards, one of the state’s prettiest parks, and a picture-perfect downtown rich in vintage quilts and antiques, gourmet foods, clothing, and arts and crafts.

  • Dream Date: Start the day off with a tour of Lanier Mansion and its amazing gardens, followed by lunch at The Attic and Coffee Mill Café — don’t miss the caramel apple pie for dessert! Work it off by visiting downtown’s shopping district for its many specialty shops, galleries, and cafes, including All Good Things, which has lovely handmade soaps and lotions for your sweetie. Then visit the Thomas Family Winery for a sip inside their cozy historic carriage house. Stroll (or sway) along the river to the Key West Shrimp House, for riverfront dining in a 19th-century button factory. Follow that with a romantic horse-drawn carriage ride and a stop at Cocoa Safari Chocolates to indulge in its beautifully made and tasty chocolates. Collapse into bed at the Iron Gate Inn, or one of the other lovely B&B’s in Madison’s historic district.

Natchitoches Louisiana Couple in ParkNatchitoches, Louisiana. With its historic brick thoroughfare, picture-book architecture, and Southern-style charm, Natchitoches is sure to delight, whether through its regional arts and antiques, cozy restaurants, or its stunning Virginia Baker Park — a favorite location to tie the knot.

  • Dream Date: Start on Front Street, a brick thoroughfare that is more than 100 years old.  Browse many of the unique stores in the downtown area including The Book Merchant, Natchitoches Art Guild and Gallery, and Kaffie-Frederick General Mercantile, the oldest existing hardware store in Louisiana. Freshen your hair and makeup, or indulge in a massage at Rejuvenation Medical Spa. Meander along the banks of Cane River Lake and find yourself in Virginia Baker Park. Its garden and water feature offers a perfect spot to tie the knot, if you haven’t already. For dinner, eat at one of the Historic District’s many locally owned restaurants, such as The Landing Restaurant & Bar where you can dine by candlelight while overlooking Front Street and Cane River Lake. An after-dinner carriage ride will dazzle you with the region’s rich history and beautiful historic homes, featured prominently in the beloved movie, "Steel Magnolias.” Fall into bed at the award-winning Queen Anne B&B, or one of several other bed and breakfasts that offer double Jacuzzi tubs, scrumptious breakfasts and lovely gardens. For more ideas on visiting the area, download their free iTunes app.

Franklin Tennessee Bride & GroomFranklin, Tennessee. Franklin’s historic downtown has been stealing hearts for years, especially its 73-year old theatre, the “home of first kisses"; its quaint sidewalk cafes; and colorful Victorian architecture.

  • Dream Date: Start your memory-making at one of Downtown Franklin's historic churches with a wedding ceremony — or perhaps just a visit. Browse the antique Art Deco rings from Walton's Estate Jewelry and round out your home wares with a trip to The Registry on Main Street. Escape for some pampering at Serendipity Spa, then pick out the perfect dress for dinner at Haven, while he finds a sportcoat at F.M. Allen. Dine at Puckett's Grocery & Restaurant for their prime rib and shrimp and grits, and a live show of Nashville songwriters over a bottle of wine. After the show, window shop along Main Street, enjoying the nostalgic toys at Main Street Toys and the spring herb garden essentials at Yarrow Acres. Gear up at Bink's Outdoor Outfitters for your next adventure vacation, then pop in to Red Pony Restaurant for a marquee martini, or Sweet CeCe's for a frozen yogurt. Finally, break out the fizzy Hullaballoo bath balls from Bathos and a scented candle from Philanthropy and enjoy a romantic evening at one of Franklin's charming inns.

Paducah Kentucky RiverboatPaducah, Kentucky. Lovers can do no better than visit Paducah, with its horse-drawn carriage rides along cobblestones streets, one-of-a-kind restaurants in historic treasures, and lovely riverfront setting.

  • Dream Date: Visitors should fuel up for the day on delectable quiche and pastry at Kirchhoff’s, a fifth-generation deli and artisan bakery located in the family’s ancestral home at historic Market House Square. Grab a coffee or bubble tea at Etcetera Squared, an offshoot of a popular coffeehouse offering “killer beans and fine teas.” The day’s adventures should include a visit to the National Quilt Museum — these are not your grandmother’s quilts! — and its gift shop filled with fine local and regional crafts. The many galleries and art studios downtown are other must-sees, followed by a romantic stroll along the river to catch a classic film at the playfully named Maiden Alley Cinema. Afterwards. stop for dessert at the Chocolate Factory, an old-fashioned candy and cake supply store that sells handmade chocolates and nostalgia by the pound. Finally, enjoy a night at Fox Briar Inn at Riverplace. Located in the heart of downtown, it offers a stunning river view.

Whether strolling down cobblestone streets with your honey, toasting your anniversary with a local wine, or scouting for your perfect wedding locale at gorgeous country mansions, these Main Street communities are the perfect backdrop for it all.

To see captions for the slideshow at the top of this page, click on the pictures to view photo information in flickr. Or you can use the full screen slideshow view by clicking the lower black bar under the photos, then clicking the icon that has four arrows on it at the right side of the box, and then choosing to show the caption information from the Options menu.

Now its Your Turn! Have you had a memorable experience in these romantic places? Or tell us about a Main Street town or neighborhood you've fallen in love with...


This story is closed to new comments.

Submitted by Giggle at: March 24, 2011
I, too, grew up in Natchitoches and lived there for the past 10 years as an adult. It is truly a beautiful town with much history. I have never known a person who visited who wasn't enchanted by the town.

Submitted by TJ at: February 25, 2011
Madison, Indiana is nice...Middletown, Connecticut is nice as well...good choices. The campus of Wesleyan University is very scenic.

Submitted by Jaime at: February 23, 2011
Middletown is a good size city, with suburb living and urban apartments. Good options for schooling as well, since there are 4 high schools in Middletown. Wesleyan...what a beautiful campus! Congrats!

Submitted by Michael Jordan at: February 22, 2011
Wesleyan University is the greatest.

Submitted by Len at: February 22, 2011
Main Street in Middletown, CT is just beautiful anytime of the year! Such a revitalization within the last decade. There is such diversity and unique charm downtown. Middletown was actually named one of the top 100 place to live a few years back I think.

Submitted by Gnow at: February 17, 2011
I fell in love with Middletown the first time I saw the place. My son was attending Wesleyan University for the first time and the beauty of the place made it easy for a mother to release her son who was leaving home for the first time....Beautiful place..Middletwon, CT

Submitted by DMS at: February 15, 2011
Madison, IN is also a big dog town! We love to take our dogs walking on the river walk, hiking @ Clifty State Park & to the cutest dog boutique on Main Street called The Blue Cerebus. The Riverboat Inn allows dogs to stay also. Great place for people & pups!

Submitted by Anonymous at: February 15, 2011
I do not see how Main St. in Middletown CT could be the most romantic when they openly have prostitutes at one end of Main St. This makes no sense!!!

Submitted by sprite at: February 14, 2011
Ah, how I miss Middletown, Conn. Great choice to kick off the post!

Submitted by tjkickie at: February 14, 2011
We were married in Madison, IN in June. It is definitely romantic! We love the Lanthier Winery and the Lottie Mae B&B, The Riverboat Inn is great too. Everyone - guests and locals - hang out on the back deck in the evening listening to a guitar player and getting to know each other. It's great!

Submitted by Benjamin Dewhurst at: February 14, 2011
We actually filmed an entire romance in Madison, IN due to the romantic nature of the town! Recently premiered at an IMAX, and likely to show there!

Submitted by Raven at: February 14, 2011
My daughter was married on New Year's Day at the Inn at Middletown. It was really lovely. Middletown has a beautiful Main Street and much more to offer with hundreds of restaurants to chose from. Thank you for including us in your list.

Submitted by Alli at: February 13, 2011
Skaneateles, NY...stunning

Submitted by Fogged In at: February 13, 2011
Have you ever been to Nantucket, MA?

Submitted by Mike at: February 12, 2011
I actually propsed to my wife on main street in Franklin, TN in front of the old court house! We now live 5 mins from that spot! It's a picture-perfect setting and the restored theatre with replica vintage marquee is a nice touch!

Submitted by preservation4us at: February 11, 2011
Madison is a beautiful surprise to those who visit. Some come back over and over. Others find that they HAVE to move here to enjoy it year-round!

Submitted by KAC at: February 11, 2011
Savannah should be on the list. They have proposals and weddings in all the squares!

Submitted by Nonnie at: February 11, 2011
I am from Natchitoches, and it is great to see it recognized! The downtown area, particularly Front Street really is beautiful. Thank you for putting a spotlight on it!