Preheat your oven to 375°F (190°C). Halve the sugar pumpkin, scoop out seeds, and place cut-side down on a lined baking sheet. Roast for 45-60 minutes until tender.
Once cooled, scoop out the flesh and blend until smooth.
Rim your glass with a mixture of sugar and pumpkin pie spice.
In a shaker, combine tequila, lime juice, pumpkin puree, agave nectar, and pumpkin pie spice with ice. Shake well for about 15-20 seconds.
Strain into the prepared glass filled with ice and garnish with cinnamon sticks or orange slices.