Multiwavelength observations of the high-frequency-peaked blazar 1ES 2344+514 were performed from 2007 October to 2008 January . The campaign represents the first contemporaneous data on the object at very high energy ( VHE , E > 100 GeV ) \gamma -ray , X-ray , and UV energies . Observations with VERITAS in VHE \gamma -rays yield a strong detection of 20 \sigma with 633 excess events in a total exposure of 18.1 hours live-time . A strong VHE \gamma -ray flare on 2007 December 7 is measured at F ( > 300 GeV ) = ( 6.76 \pm 0.62 ) \times 10 ^ { -11 } ph cm ^ { -2 } s ^ { -1 } , corresponding to 48 % of the Crab Nebula flux . Excluding this flaring episode , nightly variability at lower fluxes is observed with a time-averaged mean of F ( > 300 GeV ) = ( 1.06 \pm 0.09 ) \times 10 ^ { -11 } ph cm ^ { -2 } s ^ { -1 } ( 7.6 % of the Crab Nebula flux ) . The differential photon spectrum between 390 GeV and 8.3 TeV for the time-averaged observations excluding 2007 December 7 is well described by a power law with a photon index of \Gamma = 2.78 \pm 0.09 _ { stat } \pm 0.15 _ { syst } . On the flaring night of 2007 December 7 the measured VHE \gamma -ray photon index was \Gamma = 2.43 \pm 0.22 _ { stat } \pm 0.15 _ { syst } . Over the full period of VERITAS observations contemporaneous X-ray and UV data were taken with Swift and RXTE . The measured 2–10 keV flux ranged by a factor of \sim 7 during the campaign . On 2007 December 8 the highest ever observed X-ray flux from 1ES 2344+514 was measured by Swift XRT at a flux of F ( 2–10 keV ) = ( 6.28 \pm 0.31 ) \times 10 ^ { -11 } erg cm ^ { -2 } s ^ { -1 } . Evidence for a correlation between the X-ray flux and VHE \gamma -ray flux on nightly time-scales is indicated with a Pearson correlation coefficient of r = 0.60 \pm 0.11 . Contemporaneous spectral energy distributions ( SEDs ) of 1ES 2344+514 are presented for two distinct flux states . A one-zone synchrotron self-Compton ( SSC ) model describes both SEDs using parameters consistent with previous SSC modeling of 1ES 2344+514 from non-contemporaneous observations .