After the construction of a fortress in 1211, Luki gained strategic importance, defending the approaches to Pskov and Novgorod.

[2] It was besieged and captured by Polish-Lithuanian King Stephen Báthory in 1580, and remained under Polish control until 1582.

On 1 August 1927, the uyezds were abolished, and Velikoluksky District was established, with the administrative center in Velikiye Luki.

During World War II, in 1941 and 1942, fighting took place in the vicinity between German and Soviet forces.

[15] During the Battle for Velikiye Luki (in late 1942), a German force of about 20,000 was surrounded in the town which had been turned into a fortress.

A significant portion of the Soviet forces fighting on Velikiye Luki consisted of Estonians mobilized to the Red Army, and approximately 6000 of them died liberating the town.

[14] In 2016, Velikiye Luki celebrated the 850th anniversary of the town's first appearance on historical sources, which is dated to 1166.

The town marked the event with festivals and historical exhibitions, as well as making long-term improvements.

Russian Prime Minister Dmitry Medvedev offered federal support to the anniversary, and recommended the Ministry of Transport fund a much-needed overpass connecting the two busiest parts of Velikiye Luki.

[18] Among the improvements planned was the remodel of a large obelisk in Jubilee Square, which was erected on the city's 800th anniversary in 1966 but never finished (and had been dubbed a "white elephant").

Another railway, running to the northwest, connects Velikiye Luki via Toropets and Ostashkov with Bologoye.

The two museums in Velikiye Luki are the Velikiye Luki Local Museum, which exhibits collections of local interest,[25] and Ivan Vinogradov Museum-House, located in the house which belonged to the parents of mathematician Ivan Vinogradov.

[26] There are several institutions of higher education in the city: Velikiye Luki is notable for ballooning competitions, which are held in the town annually since 1996.

Modest Mussorgsky's memorial house in Kunyinsky District, standing on the bank of a large picturesque lake, is within easy range of the town.