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Plovdiv has all the services and attractions of a major population centre, but it especially takes pride in its old town.
BBC: Bulgarian road trip: Sofia to the City of the Tsars
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In 1943, German forces took 8, 500 Jews to a square in the Bulgarian city of Plovdiv in preparation for deportation to death camps in Poland.
BBC: Bulgaria regrets failing to save thousands of Jews in WWII
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Emerging from the winding mountain road, full of cliffs and stunning vistas, one reaches Asenovgrad, noted for its wineries, before arriving at Plovdiv, Bulgaria's second (and arguably best) city.
BBC: Bulgarian road trip: Sofia to the City of the Tsars
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Middlesbrough defeated FC Xanthi to secure their passage to the group stage, while a late goal from Kevin Nolan ensured Bolton saw off the challenge of Bulgaria's Lokomotiv Plovdiv.
BBC: SPORT | Football | Europe | Boro & Bolton learn Uefa Cup fate
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From Plovdiv, take the E85 back road 108km straight north to Kazanlak, an eccentric, agricultural destination where an interesting mix of Bulgarians, Roma and ethnic Turks congregate in the town's gregarious open market.
BBC: Bulgarian road trip: Sofia to the City of the Tsars