60 wildflowers were recorded blooming in Massachusetts in May in our iNaturalist sample; 39 of the top 50 are at their peak this month. The list is ranked by number of research-grade observations.
Top wildflowers in May

Northern Starflower

Pink Lady's Slipper

Azure Bluet
Wood Anemone
Wild Geranium

Canada mayflower
Garlic Mustard

Fringed Polygala

Red Trillium

Beach Plum

Red Columbine

Jack-in-the-Pulpit
All wildflowers blooming in Massachusetts in May
| # | Species | Scientific name | Family | Obs. | Peak in state |
|---|---|---|---|---|---|
| 1 | Northern Starflower | Lysimachia borealis | primrose family | 1,803 | May (peak) |
| 2 | Pink Lady's Slipper | Cypripedium acaule | Orchids | 1,732 | May (peak) |
| 3 | Azure Bluet | Houstonia caerulea | madder family | 958 | May (peak) |
| 4 | Wood Anemone | Anemonoides quinquefolia | buttercup family | 741 | May (peak) |
| 5 | Wild Geranium | Geranium maculatum | Geranium family | 553 | May (peak) |
| 6 | Canada mayflower | Maianthemum canadense | agave and allies | 501 | May (peak) |
| 7 | Garlic Mustard | Alliaria petiolata | mustard family | 423 | May (peak) |
| 8 | Fringed Polygala | Polygaloides paucifolia | milkworts | 423 | May (peak) |
| 9 | Red Trillium | Trillium erectum | Herb-Paris, False Hellebores, Trilliums and allies | 403 | Apr (past peak) |
| 10 | Beach Plum | Prunus maritima | rose family | 398 | May (peak) |
| 11 | Red Columbine | Aquilegia canadensis | buttercup family | 375 | May (peak) |
| 12 | Jack-in-the-Pulpit | Arisaema triphyllum | Arum Family | 326 | May (peak) |
| 13 | Painted Trillium | Trillium undulatum | Herb-Paris, False Hellebores, Trilliums and allies | 324 | May (peak) |
| 14 | Sessile Bellwort | Uvularia sessilifolia | Bellworts and allies | 317 | May (peak) |
| 15 | Greater celandine | Chelidonium majus | Poppy Family | 303 | May (peak) |
| 16 | common star-of-Bethlehem | Ornithogalum umbellatum | agave and allies | 293 | May (peak) |
| 17 | European lily of the valley | Convallaria majalis | agave and allies | 279 | May (peak) |
| 18 | Ground-Ivy | Glechoma hederacea | Mint Family | 259 | Apr (past peak) |
| 19 | Wild Sarsaparilla | Aralia nudicaulis | ivy family | 250 | May (peak) |
| 20 | Annual Honesty | Lunaria annua | mustard family | 245 | May (peak) |
| 21 | Marsh Marigold | Caltha palustris | buttercup family | 244 | Apr (past peak) |
| 22 | Dwarf Ginseng | Panax trifolius | ivy family | 240 | May (peak) |
| 23 | Black Cherry | Prunus serotina | rose family | 222 | May (peak) |
| 24 | Moss Phlox | Phlox subulata | phlox family | 177 | May (peak) |
| 25 | Autumn Olive | Elaeagnus umbellata | oleaster family | 172 | May (peak) |
| 26 | Creeping Foamflower | Tiarella stolonifera | saxifrage family | 157 | May (peak) |
| 27 | Carpet Bugle | Ajuga reptans | Mint Family | 150 | May (peak) |
| 28 | Lesser Periwinkle | Vinca minor | Dogbane Family | 147 | Apr (past peak) |
| 29 | Solomon's plume | Maianthemum racemosum | agave and allies | 146 | May (peak) |
| 30 | Threeleaf Goldthread | Coptis trifolia | buttercup family | 135 | May (peak) |
| 31 | Canada toadflax | Linaria canadensis | Plantain Family | 131 | Jun (rising) |
| 32 | Yellow Star Grass | Hypoxis hirsuta | Stargrasses and allies | 129 | May (peak) |
| 33 | Yellow Trout Lily | Erythronium americanum | lily family | 128 | Apr (past peak) |
| 34 | Large White Trillium | Trillium grandiflorum | Herb-Paris, False Hellebores, Trilliums and allies | 126 | May (peak) |
| 35 | Dame's Rocket | Hesperis matronalis | mustard family | 123 | May (peak) |
| 36 | Bluebead Lily | Clintonia borealis | lily family | 121 | May (peak) |
| 37 | Trailing Arbutus | Epigaea repens | heath family | 120 | Apr (past peak) |
| 38 | Bird's Foot Violet | Viola pedata | Violet Family | 116 | May (peak) |
| 39 | golden Alexanders | Zizia aurea | carrot family | 107 | May (peak) |
| 40 | Virginia strawberry | Fragaria virginiana | rose family | 105 | May (peak) |
| 41 | Red Deadnettle | Lamium purpureum | Mint Family | 104 | Apr (past peak) |
| 42 | Lowbush Blueberry | Vaccinium angustifolium | heath family | 98 | May (peak) |
| 43 | Alder Buckthorn | Frangula alnus | buckthorn family | 97 | Jun (rising) |
| 44 | Rock Harlequin | Capnoides sempervirens | Poppy Family | 93 | May (peak) |
| 45 | One-Flowered Cancer-Root | Aphyllon uniflorum | broomrape family | 93 | May (peak) |
| 46 | Hobblebush | Viburnum lantanoides | elder family | 89 | May (peak) |
| 47 | Lesser Celandine | Ficaria verna | buttercup family | 88 | Apr (past peak) |
| 48 | Bearberry | Arctostaphylos uva-ursi | heath family | 87 | May (peak) |
| 49 | Common Dandelion | Taraxacum officinale | Sunflowers, Daisies, Asters, and Allies | 81 | Apr (past peak) |
| 50 | Herb Robert | Geranium robertianum | Geranium family | 79 | May (peak) |