18 breakfast and coffee stops inside Winchester city limits, most within a few blocks of the Loudoun Street Mall, with hours from each one's own site.
Last checked 2026-10-20. Refreshed every three months.
Most of Winchester’s coffee shops and breakfast counters are in Old Town, on the Loudoun Street Mall and on Piccadilly Street a block north. The early openers, the chains and the drive-thrus are on Pleasant Valley Road, Valley Avenue and Berryville Avenue. For weekend brunch menus, see our brunch list.
How we made this list. The places come from OpenStreetMap records inside Winchester’s city limits, the same data behind our local directory, checked against each place’s own website on 2026-10-20. Espresso Bar and Cafe and Tropical Island Coffee and Cafe have no working website; both are kept because the Friends of Old Town directory lists them, and Mimi’s Amherst Diner is kept on an October 2026 record in the Virginia Department of Health inspection database. The list is alphabetical. It is not a ranking or a recommendation, and nobody paid to be on it. Run one of these places? Write to us to correct your entry.
The list
| Name | Address | Hours as published | Phone |
|---|---|---|---|
| Big L’s Bagels | 38 E. Piccadilly St. | 7 to 11 a.m. Monday and Wednesday to Friday; 8 a.m. to noon Saturday; 8 to 11 a.m. Sunday; closed Tuesday | Not listed |
| Biscuits and Beans Cat Cafe | 185 N. Loudoun St. | 10 a.m. to 6 p.m. Monday, Tuesday and Thursday; 10 a.m. to 7 p.m. Friday and Saturday; 10 a.m. to 5 p.m. Sunday; closed Wednesday | 540-692-6184 |
| Bonnie Blue Southern Market and Bakery | 334 W. Boscawen St. | 8 a.m. to 4 p.m. Monday to Thursday; 8 a.m. to 8 p.m. Friday; 8 a.m. to 4 p.m. Saturday and Sunday | 540-686-7490 |
| Bro Bears Drive-Thru Coffee | 1141 Berryville Ave. and 2004 S. Pleasant Valley Road | 7 a.m. to 4 p.m. Monday to Friday; 8 a.m. to 5 p.m. Saturday and Sunday | 540-450-5691 |
| Dunkin’ | 1208 Berryville Ave. | 4 a.m. to 8 p.m. daily | 540-667-7456 |
| Dunkin’ | 2605 Valley Ave. | 5 a.m. to 11 p.m. daily | 540-662-0738 |
| Dunkin’ | 303 W. Boscawen St. | 5 a.m. to 8 p.m. daily | 540-662-7622 |
| Espresso Bar and Cafe (no website) | 165 N. Loudoun St. | Not posted | Not listed |
| Hideaway Cafe | 141 S. Loudoun St. | 9 a.m. to 2 p.m. Monday; closed Tuesday; 9 a.m. to 5 p.m. Wednesday to Saturday; 9 a.m. to 4 p.m. Sunday | 540-450-0799 |
| Hopscotch Coffee and Records | 250 Millwood Ave. | Not posted on its site | 540-514-5356 |
| Knead Bread | 28 E. Piccadilly St. | 6 a.m. to 5:30 p.m. daily | 540-450-5982 |
| Mimi’s Amherst Diner (no website) | 334 Amherst St. | Not posted | Not listed |
| Papermill Place | 2214 Papermill Road | 7 a.m. to 2 p.m. daily | 540-667-1136 |
| Piccadilly Grill | 46 E. Piccadilly St. | 7 a.m. to 3 p.m. Monday to Saturday; closed Sunday | 540-336-1042 |
| Starbucks | 1690 S. Pleasant Valley Road | 4:30 a.m. to 9:30 p.m. Monday to Saturday; 5 a.m. to 9:30 p.m. Sunday | 540-686-2144 |
| Tropical Island Coffee and Cafe (no website) | 39 W. Piccadilly St. | Not posted | Not listed |
| Waffle House | 1805 S. Pleasant Valley Road | Open 24 hours | 540-542-6154 |
| Water Street Kitchen | 2 S. Loudoun St. | Not posted on its site | 540-313-4680 |
The places
Big L’s Bagels makes its bagels in-house and takes online orders for pickup. It is a morning-only shop and closes by noon.
Biscuits and Beans Cat Cafe on the mall serves locally roasted coffee and fresh-baked goods, with a separate cat lounge of adoptable cats that is open from noon by reservation.
Bonnie Blue Southern Market and Bakery serves breakfast every day in a former gas station, with eggs, biscuits and gravy and house-smoked meats on its breakfast menu.
Bro Bears Drive-Thru Coffee is veteran-owned and family-run, open since 2018, with hand-crafted espresso drinks, cold brew, smoothies and sugar-free options at two drive-thru windows.
Dunkin’ has three stores inside the city: on Berryville Avenue near Interstate 81, on Valley Avenue and on West Boscawen Street near Old Town.
Espresso Bar and Cafe is a coffee shop on the mall listed in the Friends of Old Town directory. We could not find a website of its own.
Hideaway Cafe is a family-owned coffee shop at the south end of the mall that calls itself “Coffee ‘Till Cocktails.” It offers DoorDash orders and weekday curbside pickup.
Hopscotch Coffee and Records on Millwood Avenue is a coffee shop with a record store attached.
Knead Bread is an artisan bakery that makes breads, pastries, breakfast and lunch sandwiches and focaccia pizza from scratch.
Mimi’s Amherst Diner is at 334 Amherst St., west of Old Town. It has no website; an October 2026 state inspection is on record under this name at this address.
Papermill Place has been family-owned since it opened. It serves breakfast all day, with lunch from 11 a.m., and carryout at all hours.
Piccadilly Grill is a diner on East Piccadilly Street serving breakfast and lunch; its site takes reservations by phone.
Starbucks at 1690 S. Pleasant Valley Road is the company-run cafe inside the city limits. There is also a Starbucks counter inside the Target on Legge Boulevard.
Tropical Island Coffee and Cafe across from Handley Library is listed in the Friends of Old Town directory. Its old web address is now a domain for sale.
Waffle House on South Pleasant Valley Road is open around the clock.
Water Street Kitchen on the mall serves breakfast all day beside Southern plates and sandwiches, with patio seating facing the mall.
More lists
Brunch, bakeries, ice cream and desserts, all our eating lists, the local directory and restaurant inspections.
Frequently asked questions
Where can I get breakfast in Winchester?
Papermill Place on Papermill Road serves breakfast all day from 7 a.m. daily, Piccadilly Grill opens at 7 a.m. Monday to Saturday, Water Street Kitchen serves breakfast all day on the mall, and Waffle House on South Pleasant Valley Road is open 24 hours.
What is the earliest coffee in Winchester?
The Dunkin’ on Berryville Avenue lists 4 a.m. daily, the Starbucks at 1690 S. Pleasant Valley Road opens at 4:30 a.m. Monday to Saturday, and Waffle House never closes. In Old Town, Knead Bread opens at 6 a.m. every day.
Where are the coffee shops in Old Town Winchester?
Biscuits and Beans Cat Cafe, Espresso Bar and Cafe and Hideaway Cafe are on the Loudoun Street Mall, Big L’s Bagels and Knead Bread are on East Piccadilly Street, and Tropical Island Coffee and Cafe is on West Piccadilly Street.
Is there a drive-thru coffee shop in Winchester?
Bro Bears Drive-Thru Coffee has two windows, at 1141 Berryville Ave. and 2004 S. Pleasant Valley Road, open 7 a.m. to 4 p.m. weekdays and 8 a.m. to 5 p.m. on weekends.
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