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11 Towns Similar to Stars Hollow

Here's a roundup of 11 beautiful towns similar to the laid-back town of Stars Hollow where you'll find historic houses, fascinating architecture, and loads of arts and culture.

Countryside in Litchfield, Connecticut during foliage.

If you’re as much of a fan of Gilmore Girls as I am, you’ve probably considered packing up your life, wherever it may be, and moving to Stars Hollow.

Don’t we all want to live somewhere where there is a Luke’s Diner? There’s not much not to love about the cozy, laid-back town of Stars Hollow. We adore the quirky residents, the tightly knit community, the delightful local stores, and the annual traditions.

Unfortunately for us super fans, Stars Hollow only exists in TV land.

The fictional town was founded in 1779 with conflicting stories about how it got its name. The one legend is a romantic tale of two star-crossed lovers who were destined to never be together until some sort of cosmological phenomena involving the stars led them to each other at the spot where the town now exists. The inhabitants of Stars Hollow celebrate this event at the annual Firelight Festival.

Another legend about how Stars Hollow came to be is when a Puritan family first discovered the area while looking for somewhere to settle. They named the area Stars Hollow because of “the stars, so bright; this forest, so hollow!”

As you make your way through all of the seasons, you will get to know its fictional history and heritage. The town has a few landmarks, such as the gazebo in the town square and the statue of Casimir Pulaski.

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The creator of the series, Amy Sherman-Palladino, said that she took her inspiration from various little towns all over New England, starting with the tiny hamlet of Washington Depot. The good news is that many towns throughout Connecticut and even some further afield can give us a taste of Gilmore Girls’ life. Let’s go exploring.

Washington Depot, Connecticut

Bryan Memorial Town Hall in Washington, Connecticut.

Washington Depot has a few similarities to the town that Sherman-Palladino created in her series, such as the quaint local grocery store, Washington Food Market, which has operated in the town for over 100 years.

With a number of regular festivals and events, we’re sure to get a bit of a Stars Hollow vibe. I also love the look of The Mayflower Inn and Spa, which might give us a taste of New England, a bit like we would at The Independence or the Dragonfly Inn.

While there isn’t a Luke’s Diner, there is a Marty’s Café, a perfect place to stop for a sandwich and a cup of coffee. Or we could spend some time browsing books at The Hickory Stick Bookshop – a cornerstone store of Washington Depot for over 60 years. You can almost imagine Rory or Lane popping in at the store after school.

All things considered, Washington Depot looks like an excellent first stop for our Stars Hollow tour.

Litchfield, Connecticut

Countryside in Litchfield, Connecticut during foliage.

Reasonably close to Washington Depot is the little town of Litchfield. With its historical character, Litchfield is everything that you’d expect from a classic New England town. The inhabitants of Litchfield are incredibly proud of their heritage and are dedicated to protecting it.

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The Litchfield Land Trust, established in 1968, is one of Connecticut’s earliest land trusts and is dedicated to helping protect the “New England character” of Litchfield.

Litchfield has lots of independently owned stores and restaurants and even a cute antique shop.

West Street Grill looks like a great alternative to Luke’s Diner, albeit a bit fancier.

Fun fact: Luke actually references Litchfield in season 4, episode 11. 

New Milford, Connecticut

A waterfall with church in the center of Milford, Connecticut.

Many a Gilmore Girls fan blog has suggested that New Milford is one of the Connecticut towns that are most like Stars Hollow. A former New Milford resident even believed the show was filmed there!

They do have a lovely town gazebo and town green which is very Gilmore Girls. There’s even a church adjacent to the green and plenty of little shops and restaurants.

Canterbury School is a charming private school, which feels very “Chilton”. Even the uniforms are the same color as Rory’s school.

The town was incorporated in 1712, and Roger Sherman, one of the United States Founding Fathers, was once a resident.

Some of the top attractions in New Milford include swimming and boating on Candlewood Lake, which is the state’s largest lake. Also worth a visit is an iconic bridge at Lover’s Leep State Park and the Hunt Hill Farm Trust/Silo. Water lovers can enjoy kayaking or fishing on the Housatonic River.

Annual art-loving visitors can enjoy the Outdoor Art Festival in mid-June and the “Open Your Eyes” Artist Studio Tour, which happens in late June. In July, the Fourth of July Celebration and Carnival is a must, as is the Village Fair Day and Road Race in late July.

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Guilford, Connecticut

A house in Guilford, Connecticut.

Another town on the Stars Hollow lookalike list is Guilford. One visitor and Gilmore Girls fan suggested it reminded her of a supersized version of Stars Hollow, but without the quintessential gazebo.

With a big town green, the heart of the town is encircled by quaint shops and buildings,  just as a town square should be. The town is charming and walkable and feels somewhat removed from the busyness of the modern world.

In terms of apparent parallels to the fictional town, it has a hardware store that is very similar to Luke’s Diner, except with actual tools and not food being sold. The Guilford Food Center feels a bit like Doose’s Market and was featured in the 2012 movie Hope Springs, with Meryl Streep and Tommy Lee Jones.

There’s also a local dance studio which is a reminder of Miss Patty’s and a typical Stars Hollow type townhall. St. George Church is right next to the Town Green. All in all, Guilford has a very Stars Hollow feel, and you could almost imagine Lorelai and Rory running around.

Guilford was established in 1639, and it got its name from the Guildford parish in Surrey, England. Its Indian name is “Menunkatuck.”

Amongst its many notable citizens are Nick Fradiani, the 2015 American Idol winner: Becki Newton, the actor from Ugly Betty: and Colleen McCullough, author of The Thorn Birds.

When you’re in Guilford, you’ll want to visit Guilford Green, the historic Town Center with the museums, shops,  and restaurants we mentioned above. The Guilford Green has been voted “Best in New England”. With a whole host of annual events, Guilford is worth a visit all year round.

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Also, check out the Guilford shoreline with its marina, beaches, Grass Island Shack, and Faulkner’s Island Light House. Don’t forget about the golf course and hiking trails if you want to be a bit active. Golfers can play a few rounds of golf on one of the top-rated golf courses in New England.

A few historic house museums are worth visiting, such as the Henry Whitfield State Museum, Hyland House, Thomas Griswold, Medad Stone Tavern, and The Dudley Farm.

Kent, Connecticut

An ancient red farm in South Kent, Connecticut.

The next stop on the Stars Hollow tour is Kent, Connecticut.

Kent is a beautiful combination of old with new, quaint and chic. It is a charming little town to wander through, full of all the locally owner-operated stores you could wish for: a coffee shop, a bakery,  a deli, bookstores, restaurants, gift shops, and a drug store.

Kent is well known for its prestigious college prep schools, so you will definitely find a local version of “Chilton”.

There is plenty to eat with all the restaurants which serve dishes made from locally sourced produce. Art lovers will enjoy the galleries featuring quality contemporary and classic art.

Outdoor lovers will enjoy the river with its historic red-painted covered bridge, as well as Kent Falls and the Appalachian Trail.

There are a few fun town festivals and events, like the Gingerbread Festival during the holidays, where many of the local businesses compete in a gingerbread house contest, as well as the Kent Pumpkin Run in October.

Kent was established in 1739, named after Kent, England. Kent County in the United Kingdom was well known for its iron industry. Iron was found in this area of New England, which is why it was named Kent.  

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Amongst its many well-known citizens, both past and present, are Joe Bouchard, the founding member of the rock group Blue Oyster Cult, Ted Danson (who graduated from Kent School), Brendan Fraser, and Lynn Redgrave.

Another famous citizen was Henry Kissinger, the former United States Secretary of State.

When in Kent, you’re going to want to check out the Kent Falls State Park, the Macedonia Brook State Park, Bulls Bridge, the Eric Sloane Museum & Kent Furnace, and the Connecticut Antique Machinery Association Museum.

Wallingford, Connecticut

 Gouveia Vineyards in Wallingford, Connecticut.

Wallingford was established in 1670 and was named after Wallingford in Berkshire. Wallingford is a picturesque small town full of New England charm.

The “Chilton” of the area is Choate Rosemary Hall, a private preparatory school.

Visitors to the area will want to check out the Paul Mellon Arts Center and the Toyota Oakdale Theater, which hosts many theater productions, art exhibitions, and the Wallingford Symphony Orchestra.

In the downtown area, you’ll find a variety of restaurants and shops. During the summer months, pop in at the weekly Farmers Market and attend one of the Twilight Tunes Concerts.

Wallingford has many historic and architecturally significant homes which are worth exploring.

A few notable citizens from Wallingford include Lyman Hall, signer of the Declaration of Independence, Raoul Lufbery, the World War II flying ace, and Moses Y. Beach, inventor, and publisher.

Old Lyme, Connecticut

Gillette Castle near Lyme, Connecticut.

Old Lyme was established in 1636 and named after Lyme Regis in England.

Old Lyme is a must-visit for artists and art lovers. It is well known as an artists’ community centered on the emerging “American Impressionism” movement in the early 1900s, and you will find much of its art heritage evident in the central village on Lyme Street. Several private galleries and public buildings also celebrate this strong art heritage, and the town continues to attract many practicing artists today.

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Visitors are also attracted to the beach communities along Long Island Sound, and lovers of the outdoors, such as hikers and bird watchers, will enjoy the many trails around the town.

Among the notable citizens, past and present, are Florence Griswold and Roger Tory Petersen, the naturalist.  What is now known as the Florence Griswold Museum has been the home of the Lyme Art Colony for over a century. This is America’s center of Impressionism.

Regular summer visitors to Old Lyme included Albert Einstein and President Woodrow Wilson.

When you’re in Old Lyme, be sure to visit the Florence Griswold Museum, Lyme Academy College of Fine Arts, Lyme Art Association, and Sound View beach.

Essex, Connecticut

The historic Hayden Starkey Store in Essex, Connecticut.

Essex was incorporated in 1852, and it got its name from England’s Essex County, where some of its early settlers were from. Essex was originally called Potopaug by the indigenous people.  

Essex is one of three villages located on the Connecticut River, close to Long Island Sound. Essex is well-loved for its beautiful landscapes, gardens, fascinating architecture, culture, history, outstanding restaurants, art galleries, and antique shops. Because it is set on the Connecticut River, it is a popular boating and sailing destination for lovers of aquatic activity.

A few of the well-known citizens of Essex have included William Pratt, William Hyde, and John Lay, founding settlers.

When in Essex, don’t miss the Connecticut River Museum, the Griswold Inn, the Essex Steam Train and Riverboat, Ivoryton Playhouse, and Pratt House.

Some of the annual events in Essex that are worth marking in your calendar are the Groundhog Day Parade in February and the Irish Parade and Festival, which takes place on the Saturday before St. Patrick’s Day in March. The Scarecrow Festival and Ivoryton Pumpkin Festival are great festivals to attend every October.

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East Haddam, Connecticut

Connecticut River along scenic Route 154 in East Haddam, Connecticut.

Haddam and East Haddam were originally one town that was named after Little Haddam in Hertfordshire, England. In 1685, the eastern part was settled. In 1734 it was incorporated as a separate town.

Like most of the other towns on this list, East Haddam allows visitors to explore New England’s history, art, and natural beauty. Spending some time in East Haddam is  an escape to the Nature Conservancy’s location called “One of the last great places.”

Enjoy East Haddam for its popular tourist attractions and outdoor recreation space, historic homes, scenic views, the preserved open space, beautiful country roads, quaint small businesses, and many other local treasures.

Nathan Hale, the American Revolutionary War patriot, and Morgan G. Bulkely, state governor and U.S. senator, are just some of the notable people who have called East Haddam home.

You will want to explore some exciting places during your visit to East Haddam include the Gillette Caste State Park, the Goodspeed Opera House, the Nathan Hale Schoolhouse, and the Connecticut River Swing Bridge.

Enjoy Music on the River on Monday evenings during July and August. These summer months also bring you outdoor theater at Gillette Castle. On the third Saturday in October, you must see the Fife & Drum Corps Ancient Muster.

Durham, Connecticut

The Church of the Epiphany of Durham, Connecticut.

Incorporated in 1708, Durham was named after the town and county in England by the same name. The indigenous people called the area “Coginchaug”.

Durham is a rural community located between Hartford and New Haven and is famous for its annual Durham Fair, which happens every fall. The popular fair has been happening since 1916 and now attracts more than 200,000 visitors every year.

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Durham’s outdoor recreation includes the Miller Pond State Park, Tri-Mountain State Park, and the Mattabesett Blue Trail. At Miller Pond, you can enjoy fishing, biking, hunting, and mountain biking. At the Tri-Mountain and Mattabesett Blue Trail, you can walk, bike, or hike  160 miles of trails.

A few of Durham’s notable citizens have included Stephen F. Austin, the founder of Texas, and Vernon “Lefty” Gomez, a New York Yankee Hall of Famer, and Vin Baker, a former NBA player for Milwaukee Bucks.

Unionville, Ontario

Brightly decorated main street of the historic village of Unionville during sunset.

A little further afield, in fact, across the border, is Unionville, Ontario, Canada. Unionville makes it onto our list because you will find the actual location for Luke’s Diner. Well, at least the Luke’s from the first season of Gilmore Girls before they moved to a studio located in Los Angeles, California. You’ll also find the church that is in one of the opening scenes of the series.

If you plan to visit Unionville any time soon, make sure you come hungry, wear comfortable shoes, and don’t forget your camera!

Main Street, Unionville, is beautiful throughout the year. It is a picturesque street lined with historic buildings, boutique shops, restaurants, spas, and salons. You will love Unionville for its amazing food – with something for everyone from Indian to Italian, Mexican to classic pub food.

There is loads of art and culture to enjoy as Main Street, Unionville hosts many multicultural events and festivals all year round. You can explore exhibits from Canadian and international artists at the Frederick Horsman Varley Art Gallery or The McKay Art Centre.

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For an escape from the hustle and bustle of the city, make your way to Toogood Pond for some well-deserved rest and relaxation. In summer, you can fish and picnic. You will need a fishing license.

In winter, the pond will have iced over so you can take it to the ice with your skates. For the active, there are also walking trails. This 33-hectare park is especially beautiful when the leaves of the trees that surround it start changing color in the fall.

If you have a sweet tooth, then Main Street, Unionville is the place for you. The Old Firehall Confectionery is your go-to for all the handmade sweets your heart could desire. Truffles, chocolates, cupcakes, fudge, ice cream, marshmallows on a stick, macarons, and candy apples are just some of the goodies you can find there.

Other Stars Hollow-like Towns Worth Checking Out

In Maine, you could visit any of the following towns for a small-town New England vibe:

  • Camden – They call themselves the ‘jewel of the coast’ for a good reason. Camden is a haven for lovers of the ocean, shoppers, and of course, outdoor adventurers. The tiny population is more than triples in the summer months with its visitors and seasonal residents.
  • Damariscotta – the little town is located near the head of the Damariscotta River, twelve miles from the ocean. This town has a thriving arts community and many beautiful houses and buildings from the Colonial period. One of the unique points of interest in Damariscotta is the oyster shell middens along the Damariscotta River. These oyster shell middens record gatherings of the indigenous people that date back more than 2,500 years!
  • Kennebunkport – The Lower Village of Kennebunk and Kennebunkport’s Dock Square can be found along the ocean and the Kennebunk River. First settled in the 1600s, it became a shipbuilding mecca, and you could often see five-masted ships and schooners trailing down the river toward the sea. The sea captains of the time built beautiful mansions, and many of these are preserved today as charming inns that give a taste of history.
  • Ogunquit – This town’s name means ‘beautiful place by the sea’ in Native American, Abenaki. Arguably one of the most beautiful places on the Southern Maine Coast, with its sandy beaches, dramatic rocky cliffs, quaint colonial architecture, and beautiful trees that line the streets, you will definitely want to visit Ogunquit.
  • Wells – a little town north of Ogunquit and south of Kennebunk is the town of Wells, founded in 1643. This little town is called the “Friendliest Town in Maine” and the Antique Capital. From beaches and shopping to nature trails and dining at any of the casual clam shacks, diners, and gourmet restaurants, there really is plenty to do and see in Wells.
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So When Are We Leaving?

Right, so we may not be able to hang out with Rory, Lorelai, and Luke, but at least we now have a very comprehensive list of tiny towns that will give us a little taste of Stars Hollow.  Where are you going to start your road trip?

References:

Travel Channel: 23 New England Towns That Might as Well Be Stars Hollow

Finding Stars Hollow: Finding Stars Hollow

Marty’s Cafe

The Hickory Stick Bookshop

Rural Intelligence: 10 THINGS TO LOVE ABOUT WASHINGTON DEPOT, CT

Washington Food Market

Town of Litchfield CT

White Memorial Conservation Center

Litchfield Land Trust

Visit Connecticut

York Durham Headwaters

Farwani Deletin: Stars Hollow – Where Was Gilmore Girls Filmed

Life at Cloverhill: SMALL TOWN ONTARIO: UNIONVILLE

Visit Maine

Kennebunkport, Maine