Hi Jessica,

Thanks for reaching out to us at the UVM Extension Master Gardener program with your question!

We reached out to UVM Entomologists, who provided the following information:

This is commonly called the speckled cutworm, Lacanobia subjuncta. This caterpillar is not often seen in Vermont, especially on tomatoes. The larvae have a wide host range, although tomatoes are not listed. Potatoes were in one citation. They have been reported to cause serious damage to apples in the state of Washington. Cutworms can vary considerably from one specimen to another in terms of color markings, which makes identification challenging. This species has been reported from two locations in northern and central Vermont. 

It is a good idea to pick off the larvae, as they likely only have one generation per year in Vermont. Scouting for the eggs earlier in the season is a good option to reduce numbers as well.

The links below provide more information about this cutworm:

https://mothphotographersgroup.msstate.edu/species.php?hodges=10299

https://treefruit.wsu.edu/crop-protection/opm/lacanobia/