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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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  28. Minnesota Fall Foliage Train Rides (2026): A Complete Guide

    Jun 11, 26 11:09 AM

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    Interested in a train ride to see the fall colors in Minnesota? Check out the North Shore Scenic Railroad in Duluth.

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  29. Kentucky Fall Foliage Train Rides (2026): A Complete Guide

    Jun 11, 26 10:10 AM

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    There are several heritage railroads in Kentucky which host excursions through the autumn season! Learn more about these trips here.

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  30. Pennsylvania Fall Foliage Train Rides (2026): A Complete Guide

    Jun 11, 26 09:54 AM

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    From the Allegheny Mountains in the west to the Pocono Mountains in the northeast, there are many spectacular fall foliage train rides in Pennsylvania.

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  31. Ohio Fall Foliage Train Rides (2026): A Complete Guide

    Jun 11, 26 09:49 AM

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    Located in the eastern Appalachian foothills, Ohio's beautiful rolling countryside offers spectacular fall colors that can be viewed by train. Learn more here.

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  32. Rhode Island Fall Foliage Train Rides (2026): A Complete Guide

    Jun 10, 26 11:35 PM

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    Enjoy the breathtaking fall colors of New England at Newport & Narragansett Bay Railroad in Rhode Island. Learn more about their trips here.

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  33. Washington Fall Foliage Train Rides (2026): A Complete Guide

    Jun 10, 26 10:49 PM

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    Learn more about locations in Washington offering fall foliage train rides. They currently include the Mount Rainier Scenic and Chelatchie Prairie railroads.

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  34. Maryland Fall Foliage Train Rides (2026): A Complete Guide

    Jun 10, 26 04:27 PM

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    View the gorgeous Appalachian Mountains by train in western Maryland via the Western Maryland Scenic Railroad. Learn more about their trips here!

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  35. Oregon Fall Foliage Train Rides (2026): A Complete Guide

    Jun 10, 26 04:23 PM

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    Discover all of the locations in Oregon hosting train rides specifically tailored towards viewing the fall colors.

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  36. Utah - Murder Mystery - Dinner Train Rides

    Jun 10, 26 01:16 PM

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    This article highlights the murder mystery dinner trains currently avaliable in the state of Utah!

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  37. Rhode Island - Murder Mystery - Dinner Train Rides

    Jun 10, 26 12:56 PM

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    Let's dive into the enigmatic world of murder mystery dinner train rides in Rhode Island, where each journey promises excitement, laughter, and a challenge for your inner detective.

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  38. Massachusetts 'Father's Day' Train Rides

    Jun 10, 26 12:46 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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  39. New Jersey 'Father's Day' Train Rides

    Jun 10, 26 12:34 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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  40. Pennsylvania 'Father's Day' Train Rides

    Jun 10, 26 12:30 PM

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    This state offers a unique way to celebrate Father's Day with unforgettable train rides that combine history, stunning landscapes, and a dash of nostalgia.

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  41. Delaware & Hudson Diesel Roster (All-Time)

    Jun 10, 26 12:18 PM

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    Long tied to Alco’s Schenectady plant on its own lines, the D&H boasted an almost exclusively Alco first-generation fleet although did settle for some GE products later on.

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  42. Tennessee - Wine Tasting - Train Rides

    Jun 09, 26 02:46 PM

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    One of the most unique and enjoyable ways to savor the flavors of Tennessee’s vineyards is by train aboard the Tennessee Central Railway Museum.

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  43. New York 'Father's Day' Train Rides

    Jun 09, 26 02:27 PM

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    If you’re looking to make this day memorable, consider taking a scenic train ride with your dad through the beautiful landscapes of New York State.

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  44. Texas "Father's Day" Train Rides

    Jun 09, 26 02:20 PM

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    In Texas, Father's Day can be made unique by combining the nostalgia and charm of train rides with the grandeur of the Texas landscape.

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  45. MBTA Unveils Heritage GP40MC-3 1776 For America 250

    Jun 09, 26 02:07 PM

    The Massachusetts Bay Transportation Authority (MBTA) has joined a growing list of railroads honoring America’s upcoming Semiquincentennial with the unveiling of its striking new heritage locomotive…

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  46. Grand Canyon Railway Unveils 'America 250' Locomotive

    Jun 09, 26 01:49 PM

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    The Grand Canyon Railway recently unveiled its own 'America 250' locomotive, F40FH #365 draped in a patriotic red, white and blue livery with the Grand Canyon flanking the rear of the engine.

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  47. CSX Unveils Two Patriotic America250 Heritage Locomotives

    Jun 09, 26 12:01 PM

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    CSX Transportation has joined the growing roster of Class I railroads honoring America’s upcoming 250th anniversary (Semiquincentennial) with the unveiling of two specially painted commemorative locom…

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  48. Union Pacific 4547 Hauls Artemis III Rocket Components

    Jun 09, 26 09:29 AM

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    In a striking display of American innovation, infrastructure, and ambition, Union Pacific’s newest commemorative locomotive, No. 4547, departed on its first revenue freight assignment, carrying solid…

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  49. Washington - Murder Mystery - Dinner Train Rides

    Jun 08, 26 12:25 PM

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    This article delves into what makes murder mystery dinner train rides in Washington State such a captivating experience.

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  50. Nevada - Murder Mystery - Train Rides

    Jun 08, 26 12:05 PM

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    Seamlessly blending the romance of train travel with the allure of a theatrical whodunit, these excursions promise suspense, delight, and an unforgettable journey through Nevada’s heart.

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