Ten long weekends dot the 2027 calendar. Most require zero vacation days. Federal holidays that land on a Monday give you Saturday to Monday off. Holidays that hit a Saturday shift to the Friday before; Sunday holidays move to Monday. That observation rule is the engine behind every three-day weekend listed here. The exceptions are Veterans Day and Thanksgiving. Both fall on a Thursday. Take a single bridge day and each becomes a four-day break.
How Federal Holidays Create Three Day Weekends
Monday holidays deliver a Saturday-to-Monday break automatically. A Saturday holiday is observed on the preceding Friday. A Sunday holiday is observed on the following Monday. The rule is mechanical, and it produces a three-day weekend every time. Private employers do not observe every federal holiday. Check your company calendar before you request time off.
January New Year's Day and MLK Day
Two long weekends open the year.
New Year's Day (Friday, January 1)
New Year's Day lands on a Friday. The weekend runs Friday January 1 to Sunday January 3. Three days. No leave required.
Martin Luther King Jr. Day (Monday, January 18)
MLK Day is fixed to the third Monday of January. In 2027 the break stretches from Saturday January 16 to Monday January 18. Book nothing. You already have the time.
February and May Presidents' Day and Memorial Day
Two Monday holidays deliver built-in long weekends.
Presidents' Day (Monday, February 15)
Presidents' Day occupies the third Monday of February. The break runs Saturday February 13 to Monday February 15.
Memorial Day (Monday, May 31)
Memorial Day closes May. It is the last Monday of the month. The weekend begins Saturday May 29 and ends Monday May 31. This is the unofficial start of summer. Campsites and beach rentals vanish early, so lock in reservations by March.
Summer Juneteenth and Independence Day
Two summer holidays create three-day weekends in June and July.
Juneteenth (Observed Friday, June 18)
Juneteenth is June 19, a Saturday. Observation pulls it to Friday June 18. The long weekend is Friday June 18 to Sunday June 20.
Independence Day (Observed Monday, July 5)
Independence Day is July 4, a Sunday. It shifts to Monday July 5. The break runs Saturday July 3 to Monday July 5. Airports heave. If you fly, depart before July 1 or on the holiday itself, when fares dip.
Fall Labor Day and Columbus Day
Two Monday holidays give you long weekends in September and October.
Labor Day (Monday, September 6)
Labor Day is the first Monday of September. The weekend spans Saturday September 4 to Monday September 6. This is the year's busiest domestic travel window. Book flights and hotels by June.
Columbus Day (Monday, October 11)
Columbus Day is the second Monday of October. The break runs Saturday October 9 to Monday October 11. Fall foliage peaks across the Northeast right around this weekend, so leaf-peeper destinations fill fast.
Year End Christmas and New Year's 2028
The final months of 2027 bring two long weekends.
Christmas (Observed Friday, December 24)
Christmas Day is December 25, a Saturday. Observation moves it to Friday December 24. The break is Friday December 24 to Sunday December 26.
New Year's Day 2028 (Observed Friday, December 31)
New Year's Day 2028 is a Sunday. It is observed Friday December 31, 2027. The long weekend runs Friday December 31, 2027 to Sunday January 2, 2028. This is the single most expensive weekend of the year to fly. Book airfare by August.
Best Bridge Days to Take Off for 2027 Holiday Weekends
Two federal holidays fall on a Thursday. Take one vacation day and each turns into a four-day weekend.
- Veterans Day (Thursday, November 11): Take Friday November 12 off. The break runs Thursday November 11 to Sunday November 14.
- Thanksgiving (Thursday, November 25): Take Friday November 26 off. The break runs Thursday November 25 to Sunday November 28. This is the busiest travel period of the year. Book everything by July.
To request these days:
- Check your work calendar for blackout dates or company closures.
- Submit a time-off request for the Friday after each Thursday holiday as early as your policy allows.
- Confirm approval before you make travel plans.