Targovishte's name comes from Slavic roots that can be interpreted as "trading place", or less literally, "market town" - this is why several settlements with almost identical names can be found all around the Balkans. Until 1934, the settlement was known as Eski Dzhumaya ('Ески Джумая'), from the Turkish Eski Cuma (or Cumayı), "Old Friday [Market]" or "Old Gathering".

Targovishte lies in a relatively flat valley in the north-eastern part of the Bulgarian Danubian Plain, between the low heights of the Ludogorie (Turkish: Deliorman) to the north-east and the Preslavska Mountain to the south-west, a part of the Predbalkan, the foothills of the Balkan Mountains. A small river, Vrana ("black" or "crow"), runs through the city before flowing into the Kamchia.

Like many Bulgarian cities, Targovishte consists of a somewhat irregular "old town" core around which more modern neighborhoods with panel-built high-rises were added in the 1970-1980s. It also has a pedestrian main street that concentrates many cafes, shops and other businesses. The pedestrian zone runs north to south, starting from a small park next to the municipal market (incl. the St. John of Rila Church), through the Vazrazhdane square (under a large electronic clock at the top of a high-rise), and reaches the city's central square before terminating at the riverside boulevard.

The area has been inhabited since prehistory - the oldest finds date back to the Neolithic era, 7-6th millennium BC. The Thracians inhabited the region in Antiquity, leaving behind their burial mounds (and the Kralevo Treasure, 3rd century BC). It was then conquered by the Roman Empire, first as a part of the province of Thracia (Thrace), then in Moesia Inferior and later, Moesia Secunda.

In the Late Antiquity and the Middle Ages, a fortified city stood on the hills south of modern Targovishte, in the area known today as Krumovo Kale ('Крумово кале', lit. "Krum's Castle", after the medieval ruler of Bulgaria). Successively held by the East Roman (Byzantine) Empire and the First and Second Bulgarian Empires, the city has been tentatively identified as Missionis, a prosperous merchant city described by the medieval Arab geographer al-Idrisi in the 12th century. The fortress was razed during the Ottoman conquest of the Balkans in the 14th century.

The modern city was established in its current location sometime in the 15th-16th century. In the 18th century, the city started holding a yearly fair for trading livestock and crafts that gradually increased in size and importance, attracting goods and merchants from foreign countries, as far as Austro-Hungary and the UK. The city suffered during the liberation of Bulgaria from Ottoman rule (1878): after the Ottoman army retreated towards Shumen, irregular troops stayed behind and started looting and burning the city, massacring almost 500 people and setting the dedicated fairgrounds on fire. After the liberation, the fair was restored with a royal decree.

After the 1940s, like elsewhere in Bulgaria the communist regime tried to develop heavy industry in the city, including a military vehicle repair plant. Industrialization had already put the fair into decline, and under a command economy its trade aspects were deemed unnecessary. Nevertheless, in the late 1980s the local government started attempts to reboot the fair as a minor industrial trade expo, like the better-known one in Plovdiv. After the fall of the regime in the 1990s, most of the city's heavy industry failed to weather the subsequent economic crisis. Today, Targovishte is an industrial town in decline that it vigorously resists: many smaller enterprises have found their niche, and a large glass factory opened in the mid-2000s, but the fair is a shadow of its former self.

Targovishte is a major station on the main line Sofia-Varna and its branches. There are multiple daily direct trains to/from Sofia (5 hours), Pleven (2.5 hours), Shumen (30-50 min) and Varna (2 hours). Going to/from Vratsa, Montana and Vidin require changing trains at Mezdra; going to Veliko Tarnovo or southern Bulgaria requires changing at Gorna Oryahovitsa; going to Ruse requires changing at Gorna Oryahovitsa or Kaspichan.

• 43.263426.5781 Railway Station (ЖП Гара) (northern end of 29-ti Yanuari Str). Old, utilitarian building that has nevertheless seen some maintenance. Unfortunately, it's a 20-min walk to downtown, mostly through an industrial area. There's a bus turnaround in front of the station: the second stop (or the first, sometimes they skip) of all the lines that stop there (3, 4 and 10) should put you within a two-minute walk to the main pedestrian street and the market. 

Targovishte is one of the stops on the Sofia - Varna route operated by Union Ivkoni/Etap Adress/Group Plus, ensuring at least two or three buses daily from each direction, including buses that may also pass through Pleven, Veliko Tarnovo, Shumen and Dobrich. There are also smaller local companies that maintain daily lines to the nearby settlements, including Omurtag, Popovo, Shumen and Razgrad.

• 43.25340626.5743572 Bus Station (Автогара, Avtogara), 5 Nikola Marinov Blvd. As usual, each company has its own ticket office within the building, so you have to find which one serves your destination. Your inner fifth-grader may be entertained by the garage of the local fire brigade that is just across the street. The bus station is on a 5- to 10-min walk to the local market and the small park that starts the pedestrian main street. 

As of early 2023, the eastern fragment of the unfinished Hemus Motorway (A2) ends 10 km (6.2 mi) east of Targovishte, at Buhovtsi; Targovishte is right on the E772 road that connects the two sections, ensuring connection to Shumen (45 km (28 mi)) and Varna (120 km (75 mi)) to the east, and Veliko Tarnovo (100 km (62 mi)), Pleven (186 km (116 mi)), and Sofia (320 km (200 mi)) to the west.

To the north, Republic road 49 connects Targovishte to Razgrad (40 km (25 mi)), merging into E70 to Ruse (100 km (62 mi)). South of Targovishte, Road 48 branches off E772 at Omurtag to cross the Balkan Mountains through the Kotel Pass into Southern Bulgaria, with connections via E871 and Motorway A1 to Sliven, Yambol and Burgas.

Even outside of the pedestrian centre, Targovishte is a compact and flat city so it's completely possible to hit all main points on foot. The exceptions are the fortress ruins and the hiking paths outside of town, which require either a car or using public transport (unless you fancy a 7 km (4.3 mi) hike just to get there).

Public transport is provided by passenger vans and mini-buses serving five lines. It's cheap, but the system is opaque to non-locals: schedules are available only online and only in Bulgarian, and no route map is available anywhere, even on OpenStreetMap. The fare is paid to the driver on boarding the vehicle; as of 2022, it was something like 0.40 лв, so make sure you have small change.

• Lines 3, 4 and 10 all start at the remote railway station and their routes overlap for the two stops necessary to reach the central part of the city.
• Line 4 starts at the railway station, zig-zags through the city and goes to the base of the wooded hills to the south, making it the only public transport allowing access to the local hiking paths and the ruins of a fortress (see below).

See also: Bulgaria § By taxi

As of early 2023, the municipally mandated limits on the price per kilometre are 0.75 – 1.50 лв for both day and night, which means that by law the allowed initial fee should be 1.50 – 2.25 лв, and the maximum dispatch fee is 2.25 лв. The only local taxi company that has bothered to have a website made is Elit Taxi ("ЕЛИТ ТАКСИ", +359 601 62030, +359 88 500 0077).

• 43.24786626.57778910 Yukya Park (парк „Юкя“) (5 min walk east of the central square). A short series of staircases leads to the top of a small hill with a view of the city; there's the city's name spelled in large letters in case you need photo proof you've been there. There used to be a statue at the top, Khan Krum (a medieval ruler of Bulgaria) on a horse, but it has been relocated to a bend on the river by the road (E772/4) south-west of the city. The park itself stretches to the south-east and has some large grassy areas suitable for things like frisbee. (updated Mar 2023)
• 43.24199826.57398611 Coat of Arms. The city's coat of arms arranged out of colored pebbles. (updated Mar 2023)

• 43.1980126.51259312 Ruins of Missionis (Krumovo kale) (7 km (4.3 mi) south-west of the centre, next to E772 (Republic road 4, in the direction of Omurtag/Sofia)). One of the 100 National Tourist Sites. Reaching it requires either a car, or using public transport (bus line 4). There's a small parking lot at the base of the hill, next to the bus stop and a restaurant; a dirt road leads to the ruins, and a hiking path (red markings) mostly follows the road, but then continues after the ruins to the Mladost Hut. Free; you might be able to arrange a (paid) guide if you ask at the History Museum in advance. (updated Mar 2023)

Just in case you happen to be in the city when it happens: the traditional spring fair/expo^{[dead link]} is held for a week in May, ending on or containing the day of the city (14 May) - for 2023, that is 8-14 May. Trade goods are sold in the halls of the Art Gallery (mostly "made in Bulgaria" light industry products like clothing, cosmetics and furniture), but the more entertaining things are outside - an arts-and-crafts bazaar, a series of music concerts on the grassy area east of the gallery, and various common fairground attractions (food, amusement rides, etc) next to the nearby stadium (south-west of the gallery). Other events organized for the fair vary year by year.

Modern Targovishte lies in the plain, several kilometers north of the western end of the small Preslavska Mountain (Preslav itself is at the base of the eastern end), and that's where most of the local hiking opportunities are (if you don't have a car). On the Targovishte side, there's a popular hiking area that starts where Republic Road 4 (E772) reaches the gap where it passes through the hills - at the parking lot of the Lovna Sreshta restaurant (see the Eat section), which can also be reached by public transport (bus line 4). A number of trails branch off the road that leads into the forest from the parking lot, but only two are marked:

• Red markings - branches off to the south-west, then at the Rotary Club shelter merges back into the dirt road leading to the ruins of Missionis; after the ruins, the path climbs to the radio towers on the Kodzhakuz peak (Коджакуз, 668 m (2,192 ft). A short road connects it to the Mladost hut (see the Sleep section; you can also eat there, or at least buy a snack or coffee).
• Green markings - at the parking lot, cross over the bridge to the east, then follow the dirt road south until you see the markings branching off to the east. The path climbs uphill, passing through the protected area Iglikina Polyana ("Primrose Glade"), then arcing to the south and terminating by the wind turbine close to the Mladost hut (follow the paved road west to the hut).

Each route can be done for an hour or two. A number of other paths are marked on OpenStreetMap and BGMountains.org (vicinity of Targovishte online; downloadable maps for Garmin with Latin place names), so if you have a GPS-enabled device you can try following other routes:

• If you want a longer hike, you can try descending from the Mladost Hut towards the village of Strazha (several possible routes, one going by a tank testing ground that's still occasionally used by the local AFV repair plant), though in that case you'll have to either walk from Strazha to Targovishte (5 km (3.1 mi)), or try your luck with public transport - there's a private shuttle bus to Targovishte, though you'll have to find where it stops (probably the main square).
• A hardcore option: following various paths and dirt roads to go along the length of the mountain all the way to Veliki Preslav, about 20 km (12 mi) as the crow flies. There are marked trails around Preslav too, and the highest point of the mountain (723 m (2,372 ft)).

If you are traveling by car, you can also try the hike to the old bridge at Stevrek (see the Nearby section below).

A small town 25 km (16 mi) south-west of Targovishte, right by the E772. Notable mostly for being the birth place of Aleksandar Aleksandrov, the second (and last, to date) Bulgarian to fly in space - in 1988, as a part of the Soviet Interkosmos programme that invited cosmonauts from friendly nations to fill the third seat in the Soyuz spacecraft.

• Aerospace Park by the road (E772)
• Cosmonaut Statue
• History Museum - has Aleksandrov's flown spacesuit.

• 43.00422926.12627713 The "Roman bridge" at Stevrek (between Targovishte/Omurtag and Elena). A picturesque old stone bridge in a remote location among the hills, though it's not actually Roman - it was built in the Ottoman era, sometime between the 16th and early 19th centuries. Reaching the village of Stevrek requires driving (or cycling) on a paved, but sometimes potholed country road; then, you have to hike to the bridge unless you have a high-clearance 4WD vehicle. To get to Stevrek from Targovishte/Omurtag: Road 408 branches off E772 30 km (19 mi) west of Targovishte (8 km (5.0 mi) west of Omurtag) - look for a bridge junction with signs to Kamburovo and (408) Stara reka, get off E772 there and follow 408 to the south (Kamburovo is in the opposite direction). Follow the 408 for 24 km (15 mi) to the south-west, passing through Iliyno ('Илийно') and a number of other villages until you reach Stevrek ('Стеврек'). Your next challenge is finding the start of the 42.99544126.1681011 Stara Reka eco-trail, because it's poorly marked - it's close to the bridge where the 408 crosses Stara Reka (the same river the old bridge is on), on the eastern side; look for a paved road starting on the north side of the street, leading uphill; there's a large faded white sign with the EU flag, and smaller, hard to notice yellow sign "Eco Trail Roman Bridge". The path is not on OpenStreetMap, but BGMountains.org has it (online map zoomed on the trail; downloadable maps for Garmin with Latin place names). (updated Mar 2023)