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Middletown, Connecticut

Everything Middletown is known for

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History of Middletown

Insurance Money and Mr. Twain RoadyGoat

Hartford has long called itself the 'Insurance Capital of the World,' and the skyline of brand-name insurers along the Connecticut River backs up the boast. But the city's most beloved address belongs to a writer. From 1874 to 1891, Mark Twain lived here in a flamboyant twenty-five-room Victorian mansion with interior touches by Louis Comfort Tiffany. These were Twain's most productive years: in this house he wrote The Adventures of Tom Sawyer, Adventures of Huckleberry Finn, and A Connecticut Yankee in King Arthur's Court. (National Geographic later named it one of the ten best historic homes in the world.) Hartford was a real publishing hub then, home to a dozen publishers, which is partly why Twain settled here in the first place. The house survives as a museum, a vivid window into the man who more or less invented the American voice.

14.1 mi away

Colt Armory

1855

Samuel Colt's revolutionary armory pioneered interchangeable parts and assembly line manufacturing, crowned by its iconic blue onion dome.

13.3 mi away

Mark Twain House

1874

Samuel Clemens lived in this elaborate Victorian Gothic home from 1874 to 1891, writing his greatest works here.

14.4 mi away

Harriet Beecher Stowe House

1871

Home of the author of Uncle Tom's Cabin, the novel that Abraham Lincoln reportedly said started the Civil War.

14.4 mi away

Goodspeed Opera House

1876

Victorian opera house on the Connecticut River that launched Annie, Man of La Mancha, and Shenandoah to Broadway.

12.0 mi away

Charter Oak Site

1687

Site of the legendary white oak tree where Connecticut's colonial charter was hidden from the English governor in 1687.

13.5 mi away

Wadsworth Atheneum

1842

Oldest public art museum in the United States, founded in 1842 by Daniel Wadsworth in Hartford.

14.0 mi away

Things to Do in Middletown

Everything Near Middletown

75 stories, landmarks & places within ~20 miles — the same local lore RoadyGoat plays as you drive through.

  • Main Street Historic District (Middletown, Connecticut) · 0.2 mi · Scraped Hmdb

    You're driving through what was once the heart of a bustling colonial port! Middletown's Main Street has been the center of community life since the earliest days of settlement. Middletown rose to prominence as a major…

  • Samuel Wadsworth Russell House · 0.3 mi · Scraped Hmdb

    Feast your eyes on this masterpiece! The Samuel Russell House, a stunning example of Greek Revival architecture, stands as a testament to a bygone era of global trade and ambition. Built in 1828, this mansion was…

  • Portland Brownstone Quarries · 1.0 mi · Scraped Hmdb

    Ever wonder where the stately brownstones of Brooklyn and Boston came from? Chances are, they came from right here. Beginning around 1846, the Portland Brownstone Quarries boomed. For decades, thousands of workers, many…

  • Connecticut Valley Hospital · 1.4 mi · Scraped Hmdb

    Prepare to be transported back in time as we explore the history of mental health treatment at Connecticut Valley Hospital, once known as Connecticut General Hospital for the Insane. The hospital's origins trace back to…

  • Connecticut Valley Hospital Cemetery · 1.7 mi · Scraped Hmdb

    Imagine a life marked not by milestones, but by a number on a stone. That's the reality for those buried in the Connecticut Valley Hospital Cemetery. Established in 1878, this cemetery served as the final resting place…

  • White-Overton-Callander House · 2.1 mi · Scraped Hmdb

    Imagine the lives of Connecticut's earliest settlers right here! This is the White-Overton-Callander House, one of Portland's oldest homes. Built around 1710 by Nathaniel White, one of Middletown's first landowners, the…

  • Indian Hill Avenue Historic District · 2.9 mi · Scraped Hmdb

    Imagine a bustling colonial village rising from the footprint of an ancient Native American settlement. That's Indian Hill Avenue. This area in Portland, Connecticut, was home to Native Americans long before European…

  • John Hollister House · 7.5 mi · Scraped Hmdb

    Pull over for a second – this unassuming house is older than you think! Dating back to 1675, this is the John Hollister House, the oldest surviving colonial structure in Glastonbury. John Hollister was one of…

  • Kimberly Mansion · 9.1 mi · Scraped Hmdb

    Right here, at the Kimberly Mansion, two sisters made a stand that echoed around the world. Abby and Julia Evelina Smith lived here and spearheaded a fascinating protest against taxation without representation. In 1873,…

  • Silas Deane House · 9.2 mi · Scraped Hmdb

    Step inside the home of Silas Deane, America's first foreign diplomat, who secretly secured French support during the Revolution. In 1776, the Continental Congress sent Silas Deane to France to solicit aid. He…

  • Hubbard Park (Meriden, Connecticut) · 9.5 mi · Scraped Hmdb

    This park is more than just a pretty view; it's a testament to one man's vision and generosity. Walter Hubbard, a local businessman, began acquiring land here in the late 19th century with the goal of creating a public…

  • Red Bridge (Meriden, Connecticut) · 10.1 mi · Scraped Hmdb

    This rare wrought iron bridge is a testament to engineering ingenuity. It's known as the Red Bridge, and it has stood here for over a century. The Red Bridge was built in 1891 by the Berlin Iron Bridge Company. Its…

Show all 75 nearby places
  • Old Wethersfield · 10.1 mi · Scraped Hmdb

    Imagine stepping back nearly four centuries! Old Wethersfield is where Connecticut's European history truly began. Back in 1634, colonists from the Massachusetts Bay Colony established a settlement here, initially known…

  • New Britain Opera House · 10.1 mi · Scraped Hmdb

    Imagine a night out in New Britain a century ago, all dressed up for the theater! This spot, where you're driving now, was once home to the New Britain Opera House, later known as the Palace Theater. Constructed in…

  • Joseph Webb House · 10.3 mi · Scraped Hmdb

    Right here, in 1781, George Washington and French General Rochambeau finalized the strategy that would ultimately lead to victory at Yorktown. In May of 1781, Washington arrived at the Joseph Webb House in Wethersfield.…

  • Lyman Viaduct · 10.3 mi · Scraped Hmdb

    Ever wondered what it's like to drive right over a buried piece of history? You're about to! Up ahead, you're literally cruising above a 150-year-old railroad trestle, the remarkable Lyman Viaduct. This isn't just any…

  • Comstock's Bridge · 10.4 mi · Scraped Hmdb

    Stop and stretch your legs at Comstock's Bridge, a charming piece of Connecticut history! This covered bridge connects East Hampton and Colchester, offering a glimpse into the past. The first bridge here was built…

  • Goodspeed Opera House · 12.0 mi · Historical Marker

    Victorian opera house on the Connecticut River that launched Annie, Man of La Mancha, and Shenandoah to Broadway.

  • Howd-Linsley House · 12.2 mi · Scraped Hmdb

    Could this be the oldest surviving building in Branford, dating all the way back to 1705? This is the Howd-Linsley House. Built around 1705, the house is a significant example of early 18th-century residential…

  • Henry Champion House · 12.3 mi · Scraped Hmdb

    Feast your eyes on this beautiful Federal-style house! It's the Henry Champion House, built back in 1790. Colonel Henry Champion, a big shot in the Revolutionary War as a commissary leader, built this place for his son,…

  • Peck, Stow & Wilcox Factory · 12.3 mi · Scraped Hmdb

    Imagine Southington bustling with the energy of its largest employer, a factory that shaped the town's identity.The Peck, Stow & Wilcox Factory, or Pexto as it was known, started here in 1870. It grew into a sprawling…

  • Goodspeed Musicals · 12.4 mi · Scraped Hmdb

    Pull over for a minute and imagine a time when East Haddam, Connecticut, was a bustling steamboat port, not just a charming riverside town. That's when the Goodspeed Opera House was born. William Goodspeed, a local…

  • Colt Armory · 13.3 mi · Historical Marker

    Samuel Colt's revolutionary armory pioneered interchangeable parts and assembly line manufacturing, crowned by its iconic blue onion dome.

  • Coltsville Historic District · 13.3 mi · Scraped Hmdb

    Imagine a world revolutionized by mass production – that's the legacy of Coltsville. Samuel Colt, a name synonymous with firearms, established his manufacturing empire here in the mid-1800s. He wasn't just making guns;…

  • Day-Taylor House · 13.3 mi · Scraped Hmdb

    Feast your eyes on one of Connecticut's finest examples of Italianate villa architecture! The Day-Taylor House, built in 1857, stands as a testament to the elegance of the mid-19th century. The house was built in 1857.…

  • Colt Armory · 13.4 mi · Scraped Hmdb

    Right here, along the Connecticut River, Samuel Colt built more than just firearms; he built an industrial empire. Colt's Armory, established in 1855, became famous for its mass production of revolvers. Colt used…

  • Charter Oak Site · 13.5 mi · Historical Marker

    Site of the legendary white oak tree where Connecticut's colonial charter was hidden from the English governor in 1687.

  • Church of the Good Shepherd and Parish House · 13.5 mi · Scraped Hmdb

    Ever wonder how grief can inspire incredible beauty? This church is proof. After Samuel Colt, the famous firearms inventor, died in 1862, his widow, Elizabeth Jarvis Colt, commissioned this stunning Episcopal church.…

  • Capewell Horse Nail Company · 13.6 mi · Scraped Hmdb

    You're looking at what was once the heart of the horseshoe nail industry! This complex was built by the Capewell Horse Nail Company after a fire destroyed their previous factory. In 1881, George Capewell invented a…

  • Noah Webster House · 13.6 mi · Scraped Hmdb

    Ever wonder where the American dictionary got its start? It was right here, near the boyhood home of Noah Webster. Noah Webster, born in 1758, spent his formative years on this very land. He went on to become a lawyer,…

  • John Barker House · 13.7 mi · Scraped Hmdb

    Pull over for a sec, because this is one of the oldest brick houses in Connecticut, built way back in 1756 for a really wealthy farmer. This is the John Barker House. John was doing pretty well for himself to afford a…

  • Wadsworth Atheneum · 14.0 mi · Historical Marker

    Oldest public art museum in the United States, founded in 1842 by Daniel Wadsworth in Hartford.

  • Hartford, CT · 14.0 mi · Local history

    Hartford, Connecticut, sits relatively flat at 59 feet above sea level, a determined place born of both promise and conflict. Its location on the Connecticut River made it a natural trading post, a hub for commerce that…

  • Hill–Stead Museum · 14.0 mi · Scraped Hmdb

    Imagine being surrounded by Monet, Degas, and Manet masterpieces in a stunning Colonial Revival mansion. That's Hill-Stead Museum. Built in 1901, this wasn't just another grand estate. It was a collaboration between…

  • First Church of Christ and the Ancient Burying Ground · 14.0 mi · Scraped Hmdb

    Step back in time at the Ancient Burying Ground, Hartford's oldest cemetery, where the stories of the city's founders lie etched in stone. This hallowed ground was formally established in 1640, serving as Hartford's…

  • Insurance Money and Mr. Twain · 14.1 mi

    Hartford has long called itself the 'Insurance Capital of the World,' and the skyline of brand-name insurers along the Connecticut River backs up the boast. But the city's most beloved address belongs to a writer. From…

  • Old State House (Hartford, Connecticut) · 14.1 mi · Scraped Hmdb

    Imagine the weight of early American democracy right here! This is the Old State House in Hartford, designed by Charles Bulfinch, and one of the oldest state houses in the U.S. Completed in 1796, this building served as…

  • Bushnell Park · 14.1 mi · Scraped Hmdb

    Step back in time as you enter Bushnell Park, a green oasis born from a pressing need. In the mid-1850s, Reverend Horace Bushnell envisioned a public space for Hartford's growing population. He recognized the importance…

  • State Arsenal and Armory · 14.1 mi · Scraped Hmdb

    Ever wondered where Connecticut's military history truly comes alive? You're looking right at it! This impressive building, the State Arsenal and Armory, has been the heart of our state's military for over a century.…

  • Bulkeley Bridge · 14.3 mi · Scraped Hmdb

    Think of the Bulkeley Bridge as Hartford's steadfast handshake across the Connecticut River, a connection that's lasted for over a century. Back in 1908, when cars were still a novelty, this bridge was built to carry…

  • Mark Twain House · 14.4 mi · Historical Marker

    Samuel Clemens lived in this elaborate Victorian Gothic home from 1874 to 1891, writing his greatest works here.

  • Harriet Beecher Stowe House · 14.4 mi · Historical Marker

    Home of the author of Uncle Tom's Cabin, the novel that Abraham Lincoln reportedly said started the Civil War.

  • Mark Twain House and Museum · 14.4 mi · Local history

    You are passing the Mark Twain House at three hundred fifty-one Farmington Avenue in Hartford, Connecticut. Samuel Clemens lived here with his wife Olivia and their daughters from eighteen seventy-four to eighteen…

  • Harriet Beecher Stowe House (Hartford, Connecticut) · 14.4 mi · Scraped Hmdb

    Pull over here for a moment. This is where Harriet Beecher Stowe, the author of *Uncle Tom's Cabin*, lived for the last 23 years of her life. Stowe moved into this cottage-style house in Hartford after already achieving…

  • Hartford Union Station · 14.4 mi · Scraped Hmdb

    Think of all the stories this place could tell. Hartford Union Station, built in 1889, has been a crossroads for travelers for over a century. It's still an active station today, serving Amtrak and CT Rail. Designed by…

  • Footguard Hall · 14.5 mi · Scraped Hmdb

    Right here, you're near the former headquarters of a guard that once protected Connecticut's governor! In 1771, the First Company Governor's Footguard was established. Their main job was to safeguard the governor and…

  • Edward W. Morley House · 14.5 mi · Scraped Hmdb

    Imagine a world where the speed of light wasn't a constant. That's what Edward Morley helped disprove right here in West Hartford! From 1906 until his death in 1923, Morley lived in this house on Westland Avenue. He was…

  • Gillette Castle · 14.8 mi · Historical Marker

    William Gillette was the most famous Sherlock Holmes of his era. He played the detective on stage over 1,300 times starting in 1899, and he invented many of the Holmes trademarks people still associate with the…

  • Old Center Burying Yard · 14.8 mi · Scraped Hmdb

    Welcome to the Old Center Burying Yard, West Hartford's oldest cemetery, a silent witness to the town's earliest days. Established in 1719, this was the only burying ground for the town's first seventy years. Many of…

  • Gillette Castle · 14.8 mi · Things to Do

    A medieval-style castle built by the actor who originated Sherlock Holmes. Secret rooms and trick locks.

  • Gillette Castle State Park · 15.0 mi · Scraped Hmdb

    Get ready to step into a real-life Sherlock Holmes mystery! This isn't Baker Street, but it's the eccentric castle dreamed up by William Gillette, the actor who famously portrayed the detective on stage. Gillette, born…

  • Lake Compounce Carousel · 15.0 mi · Scraped Hmdb

    Get ready to step back in time and take a spin on one of the oldest carousels in the country! This isn't just any ride; it's a beautifully preserved piece of amusement park history designed by the legendary Charles I.…

  • Old North Cemetery (Hartford, Connecticut) · 15.1 mi · Scraped Hmdb

    Step back in time as you pass the Old North Cemetery, a silent city holding Hartford's past. Established in 1807, it became the final resting place for many of Hartford's prominent citizens. For decades, this was the…

  • Marietta Canty House · 15.2 mi · Scraped Hmdb

    Right here, on Mahl Avenue, stands a house that was once home to a remarkable woman who made a real difference in Hartford. Marietta Canty was a talented singer and a passionate advocate for the African American…

  • Elizabeth Park, Hartford · 15.2 mi · Scraped Hmdb

    Imagine a love story so powerful, it turned a private estate into one of America's most beloved rose gardens. This is Elizabeth Park. Banker Charles M. Pond owned this land in the late 1800s. When his wife, Elizabeth,…

  • Villa Bella Vista · 15.4 mi · Scraped Hmdb

    Prepare to be transported to the Italian countryside, right here in Connecticut! Villa Bella Vista, built in 1908, is no ordinary house. Commissioned by Eila Pierre, the villa was crafted by Italian masons who…

  • Cheney Brothers Historic District · 15.4 mi · Scraped Hmdb

    Imagine a town built entirely by silk! That's essentially what you're driving through near the Cheney Brothers Historic District. In the mid-1800s, the Cheney Brothers, a family of industrialists, established their silk…

  • Sleeping Giant (Connecticut) · 15.4 mi · Scraped Hmdb

    Look out your window – you're about to meet a sleeping giant! Native Americans called this rugged mountain 'Hobbomock,' believing it was a powerful, slumbering figure. Legend says Hobbomock was a mischievous giant who…

  • Pratt, Read and Company Factory Complex · 16.2 mi · Scraped Hmdb

    Imagine the clatter of machinery and the scent of ivory – this spot was once the heart of piano key production! Pratt, Read and Company, established here in 1863, grew into a major manufacturer, processing ivory into…

  • Hammonasset Paper Mill Site · 16.7 mi · Scraped Hmdb

    Stop and imagine: this peaceful riverbank was once a bustling industrial site, the Hammonasset Paper Mill. In 1865, entrepreneurs harnessed the Hammonasset River's power to grind wood pulp and transform it into paper.…

  • Selden Neck State Park · 17.0 mi · Scraped Hmdb

    Ever wondered about Connecticut's secret islands? You're approaching one right now, a wild, boat-access-only escape on the Connecticut River. This isn't just any island; it's a piece of pristine nature preserved for…

  • Comstock-Cheney Hall · 18.3 mi · Scraped Hmdb

    Pull over here – you're near the Ivoryton Playhouse, a place that’s been putting on shows for generations! Built in 1911, it was originally Comstock-Cheney Hall, a community gathering place. Milton Stiefel bought the…

  • Fifth Camp of Rochambeau's Infantry · 18.4 mi · Scraped Hmdb

    Imagine the footsteps of Rochambeau's infantry as they marched toward the decisive battle of Yorktown. This unassuming spot in Bolton, Connecticut, known as the Fifth Camp, was a vital pause on their grueling journey.…

  • March Route of Rochambeau's Army: Bailey Road · 18.5 mi · Scraped Hmdb

    Ever wonder where French soldiers marched to help win the American Revolution? You're driving right by it! This stretch of Bailey Road is one of the best-preserved sections of Rochambeau's historic march. Imagine…

  • March Route of Rochambeau's Army: Hutchinson Road · 18.7 mi · Scraped Hmdb

    Pull over, because you're driving on a piece of living history right now! This very stretch of Hutchinson Road was a vital artery for Rochambeau's army during the American Revolution. It’s part of a network that led to…

  • Acadian House (Guilford, Connecticut) · 19.2 mi · Scraped Hmdb

    This unassuming house has a powerful story to tell: it offered refuge to those fleeing unimaginable hardship. In the mid-1750s, Acadians – French colonists from Nova Scotia – were forcibly deported by the British. Some…

  • Congregation Mishkan Israel · 19.3 mi · Scraped Hmdb

    Founded in 1840, this is the oldest Jewish congregation in New England, a testament to the enduring spirit of faith and community. In the 1840s, a group of German-Jewish immigrants in New Haven came together to form a…

  • Nathan Hale Homestead · 19.4 mi · Historical Marker

    Nathan Hale grew up in this house in Coventry, one of twelve children in a devout Puritan family. He graduated from Yale at 18, became a schoolteacher, and by all accounts was a well-liked, athletic young man. When the…

  • Jonathan Murray House · 19.4 mi · Scraped Hmdb

    Dating back to 1690, this house offers a rare glimpse into the lives of early settlers in Connecticut. It's the Jonathan Murray House, and it's one of the oldest surviving homes in the state.Built around 1690, the house…

  • Guilford Historic Town Center · 19.5 mi · Scraped Hmdb

    You’re approaching one of the best-preserved town centers in New England, a place where time seems to slow down. This town green was originally laid out in 1639. Imagine the early settlers carefully planning their…

  • Loomis Homestead · 19.5 mi · Scraped Hmdb

    Pull over for a sec, because you're about to see a piece of living history! This is the area of the Loomis Homestead, one of the oldest timber-frame houses *still* standing in America. It all started when Joseph Loomis,…

  • Heublein Tower · 19.7 mi · Scraped Hmdb

    Imagine hosting lavish parties with breathtaking views from your own private tower. That was the life of Gilbert Heublein, a Hartford spirits magnate, who built this iconic tower. Construction began in 1914, replacing a…

  • Deacon John Grave House · 19.7 mi · Scraped Hmdb

    Imagine building a house and your family living in it for THREE CENTURIES! That's exactly what happened here. Deacon John Grave, a prominent figure in early Madison, built this saltbox-style home in 1681. He and his…

  • Essex Steam Train & Riverboat · 19.8 mi · Historical Marker

    The Valley Railroad first ran along the Connecticut River in 1871, connecting Hartford to the shoreline town of Old Saybrook. For decades it hauled passengers and freight through one of the most scenic stretches of New…

  • Deacon John Moore House · 19.9 mi · Scraped Hmdb

    Dating back to 1664, this is one of the oldest houses in Connecticut. That's when Deacon John Moore built the original portion of the house you see at 37 Elm Street in Windsor. He was a prominent figure in the early…

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