Looking Forward, Looking Backward

Written by Chris Cullen on 5/19/2026

Every month is a good month to celebrate the good things and recognize all the gifts you have enjoyed in your life. It is also true that there is no bad month to take a good long look down the road and build a plan for the future.

It might be, though, that May is the one month when looking both backward and forward is most natural.

In May, if you are like most people, you realize you haven’t planned out your summer nearly enough. The drudgery of planning is an essential ingredient in creating joyous experiences. Planning now also allows for a greater degree of flexibility when unexpected changes occur, brought about by the usual suspects.

There are a lot of things to think about in May, it is both Mother’s Day month and Mental Health Awareness month, and therefore an especially good month to consider family. If you want to spend time with them this summer, you have got to lock them down now, get on their calendar. Slots fill up fast with graduations, summer camps, and their friends competing for your time.

If you are planning to stay in Maryland, you can blend coastal adventures with rich Chesapeake history. You don’t have to go far to explore a broad diversity of landscapes that perfectly balance relaxation and adventure. Here are some things to think about:

 

May 19-December 31, 2026

Ashes and Apparitions of Annapolis Ghost Tour

May 19-November 15, 2026

2 Hour Relaxing Chesapeake Day Sail on Epiphany!

St. Michaels

May 19-November 15, 2026

St. Michaels Wine Tasting Cruise on Epiphany!

St. Michaels

May 19, 2026

Quilt Square Craft Day

Darnestown

 

May 19-November 15, 2026

Beer Tasting Cruises on Epiphany!

St. Michaels

 

May 19-November 15, 2026

Half-Day Private Sail on Epiphany!

St. Michaels

 

May 19, 2026

Quilt Square Craft Day

Gaithersburg

You can see more at:

https://www.visitmaryland.org/events-calendar

 

Get to planning for your summer fun but make time to look backward as well.

May is also Memorial Day month, more than a simple long weekend or a kickoff to summer. It serves as a moment to pause and remember the men and women, and their families, who made the sacrifices to make all our summer vacations possible.

The larger lesson of the month of May, though, is to give yourself permission to dream about the future, whatever those dreams may be, and then take action to turn all those possibilities into a gratifying reality.

With MarylandSaves, we are creating opportunities for all workers in Maryland to invest in their futures, and the futures of their families. Saving for the future is hard. It means that you will do with less now, with the knowledge that a lifetime of small sacrifices begets more returns in the long run.