# Presidents & Pinot A 3-day, ~160-mile Southern road trip from Charlottesville. It chains The Constitution Route & 231 and Bull Run to the Bloody Angle. - **Days:** 3 - **Distance:** ~160 mi - **Starts in:** Charlottesville - **Themes:** History, Food - **Routes chained:** [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va), [Bull Run to the Bloody Angle](https://dixieroadtrip.com/routes/nova-civilwar) Monticello and Montpelier with the Monticello AVA poured between them, then Virginia's prettiest road north — grafting onto the Civil War loop at Orange for a battlefield chaser. ## Why this itinerary works Starting in Charlottesville, this 3-day itinerary connects The Constitution Route & 231 and Bull Run to the Bloody Angle. It suits travellers interested in barbecue, boudin, oysters & tamales; battlefields, the movement & the past. The day-by-day bases let you split roughly 160 miles into a sequence of visits rather than trying to cover every linked route end to end. Use the daily highlights to decide which places deserve your longest stops. ## Day by day ### Day 1: Charlottesville & the little mountain Monticello's first tour, Michie Tavern fried chicken, then two Monticello Trail tastings (King Family if it's polo Sunday). Downtown mall dinner. Reserve the house visit before building the tasting schedule around it, and allow time for the grounds and the history of the people enslaved here. Two wineries are an upper limit, not an obligation: designate a non-drinking driver or arrange transport. Charlottesville keeps dinner and the overnight close together before tomorrow's northbound run. Confirm winery appointments and any Sunday events directly. Highlights to consider: - **Monticello** (Charlottesville) — Jefferson's 40-year argument with a hilltop — the clock, the dumbwaiters, the garden lab, and (told straight now) Mulberry Row, where the enslaved community that ran it all lived. Book the first tour; fog burns off the valley below. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Michie Tavern** (Charlottesville) — A 1784 ordinary moved up the mountain — fried chicken and blackeyed peas served by the fire like the stagecoach just left. Touristy and completely worth it. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Monticello Wine Trail** (Charlottesville) — Jefferson's failed dream, gloriously realized two centuries late: 40+ wineries ring Charlottesville in the Monticello AVA (est. 1984) — Viognier and Cab Franc are the local language. King Family's Sunday polo and Veritas's lawn are the classics. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Barboursville Vineyards & Ruins** (Barboursville) — Virginia's benchmark winery, planted by the Zonin family in 1976 around the burned-out ruins of a mansion Jefferson designed for Governor Barbour — taste Octagon in sight of the columns. The whole state's wine story in one frame. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) ### Day 2: Barboursville → Montpelier → the 231 Octagon among the ruins at Barboursville, Gordonsville's Exchange Hotel and chicken history, Madison's Montpelier — then north on 231 through Somerset's horse country. Overnight Madison or Graves Mountain. Highlights to consider: - **Gordonsville** (Gordonsville) — The 'Fried Chicken Capital': in the rail decades after the Civil War, Black women known as waiter carriers sold platters of fried chicken through train windows here — entrepreneurship history honored with a festival each spring. The Exchange Hotel by the tracks served as a Civil War hospital; its museum is excellent and haunted, allegedly. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Montpelier** (Orange) — James Madison's house, where he spent a year reading a trunkful of books and emerged with the Constitution's architecture. The Mere Distinction of Colour exhibit on the enslaved community is among the best interpretation anywhere. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Barboursville Vineyards & Ruins** (Barboursville) — Virginia's benchmark winery, planted by the Zonin family in 1976 around the burned-out ruins of a mansion Jefferson designed for Governor Barbour — taste Octagon in sight of the columns. The whole state's wine story in one frame. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Old Somerset** (Somerset) — A crossroads of stone walls and horse farms where 231 begins its show — the Madison family's houses dot the fields; the view opens south toward Gordonsville and north to the mountains. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Madison & the 231 corridor** (Madison, VA) — Madison County calls its stretch a US top-ten scenic byway and the claim holds: open pasture to the Shenandoah ridgeline the whole run. Pull-offs are informal; cows are not impressed. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) ### Day 3: Old Rag light → Sperryville → the war Morning pastures under Old Rag, coffee in Sperryville — then choose: Skyline Drive south, or east to Cedar Mountain and Brandy Station to join the Civil War loop where it crosses your path. Highlights to consider: - **Sperryville** (Sperryville) — Galleries, a chandlery, copper-pot whisky at the distillery, and Before & After's coffee — a two-block town at Thornton Gap's foot. Skyline Drive starts ten minutes up; the Valley Pike waits over the ridge. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Cedar Mountain** (Culpeper) — August 9, 1862: Jackson — famously indifferent to gunfire — drew his sword (rusted into its scabbard, the story goes) to rally a breaking line. Preserved fields, walking trail, profound quiet. [Bull Run to the Bloody Angle](https://dixieroadtrip.com/routes/nova-civilwar) - **Old Rag View & Banco** (Banco) — The granite dome of Old Rag — Virginia's most beloved (and mobbed) summit — owns the horizon; Graves Mountain Lodge below has fed hikers family-style since forever. Apple butter weekends in fall. [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va) - **Brandy Station: Fleetwood Hill** (Brandy Station) — June 9, 1863: 20,000 horsemen in the largest cavalry battle ever fought in North America. The Graffiti House's plaster still carries soldiers' charcoal signatures from both armies — they billeted in shifts. [Bull Run to the Bloody Angle](https://dixieroadtrip.com/routes/nova-civilwar) ## Practical planning Budget an average of about 53 miles per day across the whole trip, or roughly 1.2–1.8 hours behind the wheel at an assumed 30–45 mph back-roads pace. This is a planning estimate, not a measured time for each leg: transfer days can be longer and rest days shorter. Add meal stops, tours, ferries, traffic and hikes separately; use each day's navigation link for current driving estimates. ### Overnight bases - Day 1: close together before tomorrow's northbound run - Day 2: Madison or Graves Mountain - Day 3: near Culpeper, VA ### Best season & route notes - [The Constitution Route & 231](https://dixieroadtrip.com/routes/constitution-va): October is Virginia Wine Month and peak 231 foliage; book Monticello and tastings ahead. - [Bull Run to the Bloody Angle](https://dixieroadtrip.com/routes/nova-civilwar): The NPS app's audio tours for all four Fredericksburg-area battlefields are excellent and free. ## Frequently asked questions ### How many days and miles is Presidents & Pinot? Presidents & Pinot is a 3-day trip of about 160 miles. ### Where does Presidents & Pinot start? It starts in Charlottesville. ### Which routes does Presidents & Pinot chain together? It chains The Constitution Route & 231 and Bull Run to the Bloody Angle. ### Where are the overnight bases on Presidents & Pinot? Day 1: close together before tomorrow's northbound run; Day 2: Madison or Graves Mountain; Day 3: near Culpeper, VA. ## Related itineraries - [Mosby to the Bloody Angle](https://dixieroadtrip.com/trips/nova-loop) — 3 days, ~240 mi - [The Eastern Crescent](https://dixieroadtrip.com/trips/eastern-crescent) — 15 days, ~1800 mi - [The Whole Hog](https://dixieroadtrip.com/trips/whole-hog) — 28 days, ~4300 mi --- Canonical URL: https://dixieroadtrip.com/trips/presidents-pinot Publisher: Dixie Media (Dixie Road Trip, https://dixieroadtrip.com/) Last updated: 2026-10-04