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The "Havana Special": Serving Key West Until 1935

Last revised: August 25, 2024

By: Adam Burns

The Florida East Coast Railway is fondly remembered for the numerous streamliners it either owned and operated itself (like the Dixie Flagler) or those which it ferried to cities like Miami and Fort Lauderdale (such as the City of Miami, Silver Meteor, Champion, and many others).

However, its most exotic train was not even a streamliner at all and is usually forgotten, the fabled Havana Special. This train offered passengers the chance to visit the most tropical region in the continental United States as well as the most southern point in the country. 

This was also possible thanks to the efforts of Henry Flagler and his Key West Extension, constructed during the early 20th century. 

But its purpose was not solely for passenger transportation; it was built specifically to handle a deep water port which never materialized into a booming trade center as Flagler had hoped. 

Unfortunately, the Labor Day Hurricane of 1935 destroyed the extension as well as rail service to the islands. However, it's likely a safe assumption that had the line survived into the streamliner era, those trains mentioned above would have continued further south than Miami.

In this postcard, a Florida East Coast passenger consist on Seven Mile Bridge along the Key West Extension.

History

The Florida East Coast's Havana Special has a history that is directly tied to its Key West Extension, also known as the Florida Overseas Railroad. The idea of the FEC's president, Henry Flagler, to construct such a massive project was not for passenger services to the island chain but freight.

In 1905 the United States government announced  that a new canal would be constructed in Panama to link the Atlantic and Pacific Oceans, thus opening a new trade route. Flager thus hoped to tap shipments head to and from the canal via a new port in Key West as well as to Cuba and Latin America.

Seven years after that announcement, Seth Bramson notes in his book, "Speedway To Sunshine: The Story Of The Florida East Coast Railway," the first train, carrying Mr. Flagler, arrived in Key West on January 22, 1912 and the great extension was officially opened for service soon afterwards.  

In conjunction with this event, the railroad launched the Havana Special, at first a local train serving the FEC's home territory.

Consist (1930)

Key West Extension

The Special, however, was not meant as a regional train serving only the east coast of Florida between Key West and Jacksonville. The FEC intended the train to operate up and down the U.S. eastern seaboard, almost literally the entire length.

To do so required a partnership with other lines including the Atlantic Coast Line (between Jacksonville and Richmond, Virginia), Richmond Fredericksburg & Potomac (between Richmond and Washington, D.C.), and the Pennsylvania Railroad (to New York City).

Additionally, the train offered connecting service northward to Boston and even to Havana, Cuba via the Peninsular & Occidental Steamship Company (which was also owned by Flagler).  

The entire route covered 1,523 miles to Key West and 1,596 to Havana with a complete trip requiring 42 hours either aboard train or ship (the steamships operated out of both Miami as well as Port Tampa, Key West to Havana) making the Special the longest East Coast passenger route.

Its exotic nature also made the train quite successful due both to the fact that rail service was still the most efficient means of transportation at the time and the Florida East Coast spared no expense in making sure it was a magnificent operation providing top level service. 

Another postcard featuring a Florida East Coast passenger train running the Key West Extension as it crosses Long Key Viaduct.

For instance, it was an all-Pullman affair all of the way to and from New York City with a typical consist including coaches, a lounge, a diner, six sleepers, and a parlor-observation (this varied somewhat with the other lines).  

Some of the Special's on board amenities included fine dining from the tropics such as fresh citrus fruits, local seafood, and other delicacies. The lounge car, located within the center of the train was perhaps the most interesting in the consist; it offered separate areas for men and women to relax and even included baths.  

Despite the fact that this was during the era of heavyweight, non-streamlined trains the Special was certainly one-of-a-kind.  In the 84th volume/73rd annual issue of Railway Age & Railway View (covering the period from January 1, 1928 through June 30, 1928) through service on the Havana Special, from New York to Key West, began in 1924.  

In 1930, a few years after this event, travelers were given the additional option of traveling by plane to Havana and other Caribbean destinations as the FEC worked in conjunction with the Pan American airlines to provide this service via both Miami and Key West.  

Timetable (January 14, 1933)

Read Up Time/Leave (Train #141/PRR) Milepost Location Read Down
Time/Arrive (Train #110/PRR)
10:05 PM (Dp)0.0
New York, NY (Penn Station) (ET)
6:45 AM (Ar)
10:27 PM10
Newark, NJ
6:19 AM
11:23 PM58
Trenton, NJ
11:55 PM85
North Philadelphia, PA
4:49 AM
12:05 AM (Ar)91
West Philadelphia, PA
4:39 AM (Dp)
12:07 AM (Dp)91
West Philadelphia, PA
4:38 AM (Ar)
12:41 AM118
Wilmington, DE
F 4:05 AM
1:44 AM166
Edgewood, MD
2:14 PM186
Baltimore, MD
2:43 AM
3:10 AM226
Washington, D.C. (Union Station)
1:45 AM (Dp)
Time/Leave (Train #75/RF&P) Milepost Location Time/Arrive (Train #76/RF&P)
3:35 AM (Dp)226
Washingon, D.C. (Union Station)
1:05 AM (Ar)
4:58 AM280
Fredericksburg, VA
11:36 PM (Ar)
6:20 AM (Ar)340
Richmond, VA (Broad Street Station)
10:15 PM (Dp)
Time/Leave (Train #75/ACL) Milepost Location Time/Arrive (Train #76/ACL)
6:35 AM (Dp)340
Richmond, VA (Broad Street Station)
10:00 PM (Ar)
9:15 AM (Ar)465
South Rocky Mount, NC
7:15 PM (Dp)
9:20 AM (Dp)465
South Rocky Mount, NC
7:10 PM (Ar)
9:40 AM480
Wilson, NC
11:15 AM554
Fayetteville, NC (Fort Bragg)
5:20 PM
12:57 PM (Ar)637
Florence, SC
3:40 PM (Dp)
1:05 PM (Dp)637
Florence, SC
3:32 PM (Ar)
2:55 PM732
North Charleston, SC (North Station)
1:27 PM
797
Yamassee, SC
12:13 PM
F814
Ridgeland, SC
F828
Hardeeville, SC
12:13 PM
5:17 PM (Ar)849
Savannah, GA
11:05 AM (Dp)
5:25 PM (Dp)849
Savannah, GA
10:57 AM (Ar)
6:32 PM (Ar)905
Jesup, GA
9:42 AM (Dp)
905
Jesup, GA
9:38 AM (Ar)
7:07 PM934
Nahunta, GA
9:07 AM
8:45 PM (Ar)1001
Jacksonville, FL
7:50 AM (Dp)
Time/Leave (Train #75/ACL/Tampa Sec.) Milepost Location Time/Arrive (Train #76/ACL/Tampa Sec.)
10:25 PM (Dp)1001
Jacksonville, FL
7:00 AM (Ar)
10:50 PM1014
Orange Park, FL
6:24 AM
11:00 PM1021
Doctor's Inlet, FL
6:11 AM
11:15 PM1030
Green Cove Springs, FL
5:51 AM
11:33 PM1041
West Tocoi, FL
5:34 AM
11:41 PM1046
Bostwick, FL
5:24 AM
11:55 PM1055
Palatka, FL
5:10 AM
12:18 AM1070
Pomona, FL
4:42 AM
12:25 AM1074
Huntington, FL
4:34 AM
12:28 AM1076
Crescent City, FL
4:30 AM
12:38 AM1084
Seville, FL
4:18 AM
12:45 AM1090
Pierson, FL
4:09 AM
12:51 AM1094
Barberville, FL
3:59 AM
12:58 AM1100
De Leon Springs, FL
3:50 AM
1:02 AM1103
Glenwood, FL
3:45 AM
1:09 AM1107
De Land, FL
3:35 AM
1:22 AM1113
Orange City Junction, FL
3:24 AM
F1121
Lake Monroe, FL
F
1:50 AM (Ar)1125
Sanford, FL
3:00 AM (Dp)
2:00 AM (Dp)1125
Sanford, FL
2:50 AM (Ar)
2:15 AM1135
Longwood, FL
2:20 AM1138
Altamonte Springs, FL
1140
Maitland, FL
2:25 AM
2:30 AM1143
Winter Park, FL
2:10 AM
2:55 AM1147
Orlando, FL
1:45 AM
3:22 AM1165
Kissimmee, FL
1:17 AM
3:40 AM1177
Loughman, FL
12:59 AM
F1182
Davenport, FL
3:53 AM1187
Haines City, FL
12:40 AM
4:15 AM1193
Lake Alfred, FL
12:15 AM
4:22 AM1198
Auburndale, FL
12:08 AM
4:45 AM (Ar)1208
Lakeland, FL
11:50 PM (Dp)
5:00 AM (Dp)1208
Lakeland, FL
11:40 PM (Ar)
5:25 AM1219
Plant City, FL
11:21 PM
5:37 AM1225
Dover, FL
F1228
Seffner, FL
6:15 AM (Ar)1240
Tampa, FL
10:45 PM (Dp)
Time/Leave (Train #375/ACL/Sarasota Sec.) Milepost Location Time/Arrive (Train #376/ACL/Sarasota Sec.)
6:50 AM (Dp)1240
Tampa, FL
10:00 PM (Ar)
6:58 AM1244
Uceta, FL
9:43 PM
7:14 AM1252
Remlap, FL
9:26 PM
7:27 AM1262
Ruskin, FL
9:13 PM
7:47 AM1274
Gillett, FL
8:55 PM
8:00 AM1279
Palmetto, FL
8:43 PM
8:07 AM1280
Bradenton-Manatee, FL
8:35 PM
8:15 AM1285
Oneco, FL
8:27 PM
8:21 AM1288
Matoaka, FL
8:22 PM
8:30 AM (Ar)1293
Sarasota, FL (ET)
8:15 PM (Dp)
Time/Leave (Train #37/ACL/St. Petersburg Sec.) Milepost Location Time/Arrive (Train #38/ACL/St. Petersburg Sec.)
10:00 PM (Dp)1001
Jacksonville, FL
7:05 AM (Ar)
F1020
Baldwin, FL
F
F1039
Sapp, FL
F
F1043
Ellerbee, FL
F
10:56 PM1046
Raiford, FL
5:49 AM
11:05 PM1053
Lake Butler, FL
5:40 AM
F1059
Munich, FL
F
F1062
Worthington Springs, FL
F
F1065
Santa Fe, FL
F
F1069
Haynesworth, FL
F
11:40 PM1072
Burnetts Lake, FL
5:05 AM
F1076
Hague, FL
F
F1082
Paradise, FL
F
12:07 AM1086
Gainesville, FL
4:30 AM
F1096
Rochelle, FL
F
F1101
Micanopy Junction, FL
F
F1104
Evinston, FL
F
F1105
Boardman, FL
F
12:56 AM1107
McIntosh, FL
3:39 AM
F1108
Orange Lake, FL
F
F1109
Proctor, FL
F
F1113
Reddick, FL
F
F1116
Lowell, FL
F
F1119
Martin, FL
F
F1122
Kendrick, FL
F
1:53 AM1127
Ocala, FL (Union Station)
2:50 AM
2:16 AM1141
Candler, FL
2:16 AM
2:23 AM1144
Ocklawaha, FL
2:09 AM
2:29 AM1146
East Lake, FL
2:03 AM
2:35 AM1149
Weirsdale, FL
1:58 AM
2:45 AM1153
Lady Lake, FL
1:48 AM
2:55 AM1158
Fruitland Park, FL
1:40 AM
3:07 AM1161
Leesburg, FL
1:30 AM
3:17 AM1167
Okahumpa, FL
1:17 AM
3:37 AM1176
Center Hill, FL
1:00 AM
3:47 AM1180
Webster, FL
12:51 AM
F1186
St. Catherine, FL
F
4:17 AM1191
Croom, FL
12:26 AM
4:35 AM (Ar)1200
Trilby, FL
12:10 AM (Dp)
4:40 AM (Dp)1200
Trilby, FL
12:05 AM (Ar)
5:01 AM1212
San Antonio, FL
11:41 PM
F1215
Pasco, FL
F
5:22 AM1224
Ehren, FL
11:18 PM
5:42 AM1234
Odessa, FL
10:58 PM
F1238
Keystone Park, FL
F
6:00 AM1245
Tarpon Springs, FL
10:36 PM
F1248
Crystal Beach, FL
F
6:15 AM1250
Palm Harbor, FL
10:23 PM
6:26 AM1255
Dunedin, FL
10:14 PM
6:33 AM1258
Clearwater, FL
10:06 PM
6:43 AM1259
Belleair, FL
9:56 PM
6:55 AM1263
Largo, FL
9:42 PM
F1267
Cross Bayou, FL
F
7:05 AM1269
Pinellas Park, FL
9:31 PM
F1272
Lellman, FL
F
7:25 AM (Ar)1263
St. Petersburg, FL (ET)
9:15 PM (Dp)
Time/Leave (Train #75/FEC) Milepost Location Time/Arrive (Train #76/FEC)
9:30 PM (Dp)1001
Jacksonville, FL
7:15 AM (Ar)
10:20 PM1038
St. Augustine, FL
6:20 AM
10:59 PM1088
Bunnell, FL
5:32 AM
11:21 PM1105
Ormond, FL
11:39 PM1111
Daytona Beach, FL
4:56 AM
12:05 AM (Ar)1126
New Smyrna Beach, FL
4:30 AM (Dp)
12:15 AM (Dp)1126
New Smyrna Beach, FL
4:20 AM (Ar)
F1155
Titusville, FL
3:31 AM
1:20 AM1175
Cocoa-Rockledge, FL
3:01 AM
1:51 AM1195
Melbourne, FL
2:32 AM
1229
Vero Beach, FL
1:47 AM
3:10 AM1243
Fort Pierce, FL
1:25 AM
F1262
Stuart, FL
12:47 AM
F1276
Hobe Sound, FL
12:26 AM
4:30 AM (Ar)1300
West Palm Beach, FL
11:55 PM (Dp)
4:40 AM (Dp)1300
West Palm Beach, FL
11:45 PM (Ar)
F1307
Lake Worth, FL
11:30 PM
F1318
Delray Beach, FL
11:13 PM
5:20 AM1326
Boca Raton, FL
11:01 PM
5:43 AM1342
Fort Lauderdale, FL
10:39 PM
5:58 AM1349
Hollywood, FL
10:27 PM
6:30 AM (Ar)1367
Miami, FL
10:00 PM (Dp)
7:15 AM (Dp)1367
Miami, FL
9:30 PM (Dp)
7:25 AM1372
Coconut Grove, FL
9:14 PM
7:30 AM1375
South Miami, FL
9:07 PM
7:45 AM1383
Perrine, FL
8:52 PM
7:54 AM1387
Goulds, FL
8:42 PM
7:59 AM1389
Princeton, FL
8:36 PM
8:04 AM1390
Naranja, FL
8:30 PM
8:10 AM1393
Modello, FL
8:24 PM
8:18 AM (Begin Key West Extension)1395
Homestead, FL
8:20 PM (End Key West Extension)
8:22 AM1397
Florida City, FL
8:10 PM
8:38 AM1409
Glades, FL
7:54 PM
8:49 AM (Leave Mainland)1416
Jewfish, FL
8:10 PM (Enter Mainland)
8:52 AM (Enter Florida Keys)1418
Key Largo, FL
7:42 PM (Leave Florida Keys)
9:02 AM1425
Rockharbor, FL
7:29 PM
9:12 AM1432
Tavernier, FL
7:19 PM
9:17 AM1435
Plantation, FL
7:14 PM
9:26 AM1441
Islamorada, FL (Caribbee Colony)
7:05 PM
9:47 AM1452
Craig, FL
6:44 PM
9:57 AM1458
Long Key Fishing Camp, FL
6:34 PM
10:22 AM1475
Marathon, FL (Sombrero Lodge)
6:12 PM
10:30 AM1479
Pigeon Key, FL
6:00 PM
10:54 AM1493
Big Pine, FL
5:38 PM
11:00 AM1498
Ramrod Key, FL
5:32 PM
11:10 AM1504
Pirates Cove Fishing Camp, FL
5:25 PM
11:15 AM1507
Perky, FL
5:20 PM
11:45 AM (Ar)1523
Key West, FL (ET)
5:00 PM (Dp)
Time/Leave (Peninsular & Occidental Steamship Company) Milepost Location Time/Arrive (Peninsular & Occidental Steamship Company)
12:20 PM (Dp)
Key West, FL
3:15 PM (Ar)
6:20 PM (Ar)
Havana, Cuba
9:00 AM (Dp)
Time/Leave (Pan American Airways) Milepost Location Time/Arrive (Pan American Airways)
8:00 AM (Dp)
Miami, FL
5:00 PM (Ar)
10:15 AM (Ar)
Havana, Cuba
2:45 PM (Dp)
A postcard featuring the north end of FEC's Trumbo Island Terminal in Key West, Florida during the 1920s. Trains met ships here for passengers to continue on to Havana, Cuba.

1935 Labor Day Hurricane

The Special lost much of its glamorous allure when the 1935 Labor Day Hurricane destroyed the extension forcing the train to be cutback to Miami.

According to the book, "When the Railroad Leaves Town: American Communities In The Age Of Rail Line Abandonment (Eastern United States," by author Joseph P. Schwieterman, for a time after the hurricane FEC continued dispatching the Havana Special to Key West via car ferry.

However, air and ship service continued on for 25 additional years until Fidel Castro took over the Cuban government in 1960 forcing both to be discontinued. Diesel power replaced the Class P-5a 4-6-2 Pacifics in 1942 as the FEC purchased new EMD E6s and later E7s for passenger services.  

Timetable (1930)

On October 27, 1962, what remained of the Havana Special was renamed as the East Coast Special since the train no longer offered connections to Cuba.

The name survived for only a few months for on January 23, 1963 a nasty strike was carried out by FEC's operating unions.  It paralyzed the railroad and resulted in all passenger services being discontinued.  

A postcard of Florida East Coast's main terminal at Trumbo Island in Key West, Florida where trains met ships at the dock.

Final Years

These trains returned briefly when the FEC was required to reinstate trains between Jacksonville and North Miami on August 2 1965 but this lasted only until July 31, 1968 when service ceased forever.  It's interesting to wonder how this train would have fared had the extension survived. 

For instance, consider that the Seaboard Air Line's Silver Meteor, Atlantic Coast Line's Champion, and even the Pennsylvania Railroad's South Wind all saw relatively high patronage through the 1960s with their connections to warm and sunny climate of Miami.  Could the Extension have witnessed similarly strong ridership? 

Even so, vacationers would not have been able to sustain the route, financially.  If some other means of traffic (i.e., freight) had not been found (unlikely) the Extension probably would have been abandoned even if a major hurricane, such as the 1935 storm, had not severely damaged the line. Finally, for a history of the Key West Extension please click here.

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    With thousands of tickets sold for its upcoming series of Semiquincentennial Steam Celebration excursions, Reading & Northern Railroad is also anticipating thousands more trackside spectators to bear…

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  29. Ohio 'Murder Mystery' Dinner Train Rides

    May 22, 26 11:36 AM

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    The murder mystery dinner train rides in Ohio provide an immersive experience that combines fine dining, an engaging narrative, and the beauty of Ohio's landscapes.

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  30. Tennessee 'Murder Mystery' Dinner Train Rides

    May 22, 26 11:31 AM

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    Amidst the rolling hills and scenic landscapes of Tennessee, an exhilarating and interactive experience awaits those with a taste for mystery and intrigue.

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  31. Alabama 'Father's Day' Train Rides

    May 22, 26 11:29 AM

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    Alabama, with its rich railway heritage and scenic countryside, is a wonderful way to experience by train. One location even hosts a special trip for Father's Day!

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  32. North Carolina 'Father's Day' Train Rides

    May 22, 26 11:26 AM

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    Celebrating dad on a scenic train in North Carolina can be found at the New Hope Valley Railway which hosts a special event for the day.

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  33. Texas 'Wine Tasting' Train Rides

    May 22, 26 11:25 AM

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    This article invites you on a metaphorical journey through some of these unique wine tasting train experiences in Texas.

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  34. New York 'Wine Tasting' Train Rides

    May 22, 26 11:22 AM

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    This article will delve into the history, offerings, and appeal of wine tasting trains in New York, guiding you through a unique experience that combines the romance of the rails with the sophisticati…

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  35. The Spirit of America: George H.W. Bush’s 1992 Campaign Train

    May 22, 26 11:11 AM

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    In the fading days of summer 1992, President George H. W. Bush embarked on a classic American political tradition: the whistle-stop tour.

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  36. Burlington Northern Timetables (May, 1972)

    May 21, 26 11:56 PM

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    Presented here is the Burlington Northern's condensed freight timetables from the May, 1972 edition of the "Official Guide Of The Railways."

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  37. Whiskey Tasting Train Rides (2026)

    May 21, 26 11:12 PM

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    These rides across the United States offer a sensory journey through lush landscapes and historical corridors, often pairing scenic vistas with curated whiskey tastings.

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  38. Father's Day Train Ride Locations (2026)

    May 21, 26 10:54 PM

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    Celebrate dad by train! Several heritage railroads and museums host trips honoring dads. Learn more about which locations offer such excursions.

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  39. The Chessie Safety Express: Steam-Powered Advocacy for Railroad Safety

    May 21, 26 10:44 PM

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    In the fall of 1980, a gleaming Chesapeake & Ohio (C&O) 4-8-4 steam locomotive named No. 614 thundered across the rails of the Chessie System, pulling a colorful consist of passenger cars filled with…

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  40. Frankfort and Cincinnati Railroad: "The Kentucky Midland Route"

    May 21, 26 06:08 PM

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    The Frankfort & Cincinnati was a small shortline located in north-central Kentucky that was known as "The Whiskey Route" for the many distilleries it served. The F&C shutdown in 1985.

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  41. North Carolina 'Whiskey Tasting' Train Rides

    May 21, 26 12:43 PM

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    One of the GSMR's most distinctive special events is Spirits on the Rail, a bourbon-focused dining experience built around curated drinks and a chef-prepared multi-course meal.

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  42. Connecticut 'Whiskey Tasting' Train Rides

    May 21, 26 12:42 PM

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    While the Naugatuck Railroad runs a variety of trips throughout the year, one event has quickly become a “circle it on the calendar” outing for fans of great food and spirited tastings: the BBQ & Bour…

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  43. Kansas "Dinner" Train Rides From Abilene

    May 21, 26 12:37 PM

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    If you’re looking for a heritage railroad that feels authentically Kansas—equal parts prairie scenery, small-town history, and hands-on railroading—the Abilene & Smoky Valley Railroad delivers.

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  44. Vermont "Dinner" Train Rides At Burlington

    May 21, 26 12:34 PM

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    There is one location in Vermont hosting a dedicated dinner train experience at the Green Mountain Railroad.

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  45. New Jersey "Father's Day" Train Rides

    May 21, 26 12:24 PM

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    There are a few locations in New Jersey celebrating dads with a train ride. Learn more about these unique trips here!

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  46. Massachusetts "Father's Day" Train Rides

    May 21, 26 12:16 PM

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    The Cape Cod Central is the one location in the state hosting an event just for dads, a special brunch train. Learn more here!

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  47. Historic Steam Locomotive Heads To Charleston For America250 Exhibit

    May 21, 26 11:58 AM

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    A rare piece of West Virginia industrial history, an 0-4-0F fireless steam locomotive by H.K. Porter in 1945, is being installed near the West Virginia State Capitol Complex in Charleston as part of a…

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  48. Connecticut 'Dinner' Train Rides At Essex

    May 20, 26 11:55 AM

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    Connecticut's rail heritage can be traced back to the industry's earliest days and a few organizations preserve this rich history by offering train rides. The Essex Steam Train also hosts dinner-theme…

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  49. Arkansas 'Dinner 'Train Rides On The A&M

    May 20, 26 11:54 AM

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    If you want a railroad experience that feels equal parts “working short line” and “time machine,” the Arkansas & Missouri Railroad delivers in a way few modern operations can.

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  50. Illinois 'Dinner' Train Rides At The MRM

    May 20, 26 11:52 AM

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    The Monticello Railway Museum (MRM) is one of those places that quietly does a lot: it preserves a sizable collection, maintains its own operating railroad, and—most importantly for visitors—puts hist…

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