A winter sweets itinerary in Bloomington can start at 7:30 a.m. with pastries and coffee or stretch past midnight with freshly baked cookies. These five stops offer distinct reasons to go, from Southern-style cobblers to a retro bakery with vegan treats.
For holiday gatherings, customer accounts of custom cakes and cupcakes provide useful starting points at Jenny’s Baking Co, Rainbow Bakery and Two Sticks Bakery. For a more spontaneous dessert run, Baked! and The Peach Cobbler Factory keep daily hours and offer delivery.
1. Jenny’s Baking Co — Custom cakes are the draw at Jenny’s Baking Co, where customers repeatedly praise help with designs, serving sizes and celebration orders. One reported combination—lemon raspberry swirl cake with cream cheese icing—offers inspiration for a gathering, while apple cider donut loaf supplies a smaller-scale winter treat. At 1711 N College Ave, Suite 105, the bakery serves breakfast and coffee and offers takeout and delivery; regular hours begin at 7:30 a.m. Wednesday through Saturday, ending at 12:30 p.m. Wednesday and Saturday and 1:30 p.m. Thursday and Friday.
2. Baked! — Baked! puts the decisions in your hands: choose the dough, mix-ins and toppings for cookies made to order. Diners repeatedly praise their soft texture and customization options, with lemon cookies studded with cheesecake pieces among the combinations described. The shop at 115 N Washington St offers takeout and delivery, opening daily at 9 a.m. and closing at 1 a.m. Sunday through Thursday or 3:30 a.m. Friday and Saturday.
3. The Peach Cobbler Factory — Southern-style fruit cobblers and banana puddings make The Peach Cobbler Factory a dessert-first stop, with warm peach cobbler and vanilla ice cream a natural cold-weather order. Customers also point to caramel apple and blackberry peach cobblers, and frequently praise the welcoming service. At 115 N College Ave, Suite 115, takeout and delivery are offered daily from 11 a.m.; closing time is 10 p.m. Monday through Thursday and 11 p.m. Friday through Sunday.
4. Rainbow Bakery — Rainbow Bakery pairs retro decor with vegan pastries, cakes and local drip coffee, giving this stop a different character from the late-night cookie and cobbler shops. Customers describe pistachio cardamom doughnuts and giant salted chocolate chip cookies, while custom cupcake orders—including gluten-free lavender and lemon versions—make it a useful lead for holiday gatherings. The bakery at 201 S Rogers St offers takeout Tuesday through Saturday, opening at 9 a.m. except Wednesday’s 9:30 a.m. start, with afternoon closing times varying by day.
5. Two Sticks Bakery — Pecan bars earn repeated mentions at Two Sticks Bakery, a small-scale shop serving sweet and savory pastries alongside coffee. Customers also praise hand pies and celebration cakes, including a strawberry cake with strawberry jam filling, and describe a changing pastry selection that rewards an early arrival. At 415 S Washington St, takeout hours are 7:30 a.m. to 2 p.m. Tuesday through Friday and 7:30 a.m. to noon Saturday; the bakery is closed Sunday and Monday.